Datasets:

Ivywake

/

USPTO_PRO

like 0

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: A stirred suspension of [5-[2-(4-ethoxycarbonyl-4-methyl-1-piperidyl)pyrimidin-5-yl]-2-(ethylcarbamoylamino)-1,3-benzothiazol-7-yl]boronic acid (166 mg, 0.286 mmol) in aqueous NaOH solution (2 M, 1.3 mL) was treated with excess hydrogen peroxide (27.5% aqueous solution, 0.45 mL) and kept at rt for 3 days by which time LCMS showed complete reaction. The resultant mixture was diluted with water (30 mL) and acidified by the addition of a small amount of conc. sulfuric acid. The precipitated solid was collected by filtration, washed with water (10 mL) and dried in vacuo to give Compound 26 as a white solid (102 mg, 78% yield). 1H NMR (DMSO-d6): δ 10.37 (1H, s), 8.67 (2H, s), 7.37 (1H, s), 6.85 (1H, s), 6.77 (1H, t, J=5.86 Hz), 4.30 (2H, dt, J=13.75, 4.56 Hz), 3.36 (2H, ddd, J=13.34, 9.92, 3.07 Hz), 3.22 (2H, p, J=6.69 Hz), 2.04 (2H, dt, J=13.63, 3.69 Hz), 1.42 (2H, ddd, J=13.55, 10.29, 3.91 Hz), 1.22 (3H, s), 1.13 (3H, t, J=7.19 Hz). m/z: 457 [M+H]+. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "sulfuric acid"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrogen peroxide"}], "amount": {"volume": {"value": 0.45, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "[5-[2-(4-ethoxycarbonyl-4-methyl-1-piperidyl)pyrimidin-5-yl]-2-(ethylcarbamoylamino)-1,3-benzothiazol-7-yl]boronic acid"}], "amount": {"mass": {"value": 166.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "NaOH"}], "amount": {"volume": {"value": 1.3, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "resultant mixture"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 30.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "reaction"}, {"type": "FILTRATION", "details": "The precipitated solid was collected by filtration"}, {"type": "WASH", "details": "washed with water (10 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "dried in vacuo"}], "outcomes": [{"reaction_time": {"value": 3.0, "units": "DAY"}, "products": [{"identifiers": [{"type": "NAME", "value": "Compound 26"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 102.0, "units": "MILLIGRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 78.0}}], "isolated_color": "white", "texture": {"type": "CUSTOM", "details": "solid"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: A solution of 4-(2-methoxyethoxy)aniline (0.397 g, 2.37 mmol) and pyridine (1 mL, 12.4 mmol) in DCM (3 mL) in was treated with 4-nitrophenyl chloroformate (Aldrich) (0.505 g, 2.51 mmol) added in portions (exothermic!). The pale yellow solution was stirred at RT for 5 h. The reaction mixture was partitioned between 0.5N HCl (20 mL) and DCM (30 mL). The organic phase was washed with 0.5N HCl (30 mL), saturated aqueous sodium bicarbonate (30 mL), water (30 mL) and saturated aqueous sodium chloride (30 mL). The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by silica gel chromatography (50 g, eluent: EtOAc in hexanes 10%-50%) to give 4-nitrophenyl 4-(2-methoxyethoxy)phenylcarbamate (0.57 g, 72% yield) as an off—white solid. 1H NMR (400 MHz, CDCl3) δ 8.25-8.32 (m, 2H); 7.32-7.43 (m, 4H); 6.87-6.97 (m, 3H); 4.09-4.15 (m, 2H); 3.72-3.79 (m, 2H); 3.46 (s, 3H). m/z (ESI, +ve ion) 333.0 (M+H)+. ### ORD JSON:

{"inputs": {"m1_m2_m4_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(2-methoxyethoxy)aniline"}], "amount": {"mass": {"value": 0.397, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "pyridine"}], "amount": {"volume": {"value": 1.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4-nitrophenyl chloroformate"}], "amount": {"mass": {"value": 0.505, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DCM"}], "amount": {"volume": {"value": 3.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "The pale yellow solution was stirred at RT for 5 h"}, "conditions_are_dynamic": true}, "workups": [{"type": "ADDITION", "details": "added in portions (exothermic!)"}, {"type": "CUSTOM", "details": "The reaction mixture was partitioned between 0.5N HCl (20 mL) and DCM (30 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "HCl"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "DCM"}], "amount": {"volume": {"value": 30.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "The organic phase was washed with 0.5N HCl (30 mL), saturated aqueous sodium bicarbonate (30 mL), water (30 mL) and saturated aqueous sodium chloride (30 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "HCl"}], "amount": {"volume": {"value": 30.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "sodium bicarbonate"}], "amount": {"volume": {"value": 30.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 30.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "sodium chloride"}], "amount": {"volume": {"value": 30.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "The organic phase was dried over sodium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CONCENTRATION", "details": "concentrated in vacuo"}, {"type": "CUSTOM", "details": "The crude product was purified by silica gel chromatography (50 g, eluent: EtOAc in hexanes 10%-50%)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "crude product"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "EtOAc"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "hexanes"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 5.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "4-nitrophenyl 4-(2-methoxyethoxy)phenylcarbamate"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.57, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 72.0}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 72.4}}], "isolated_color": "off-white", "texture": {"type": "CUSTOM", "details": "solid"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: Ethyl 3-[{[4-({1-[5-(4-methoxyphenyl)-2-methylfuran-3-yl]-3-methylbutyl}amino)phenyl]carbonyl}(methyl)amino]propanoate (660 mg) which is a synthetic intermediate in Example 151 was dissolved in ethanol-hexane (1:1, volume ratio), and the solution was subjected to HPLC using CHIRALPAK AD (50 mmID×500 mL, manufactured by DAICEL CHEMICAL INDUSTRIES, LTD.) and eluted with ethanol-hexane (1:1, volume ratio) as mobile phase at 30° C., a flow rate 60 mL/min. The fractions showing a peak with retention time 21.4 min were collected, and concentrated. The obtained amorphous compound (319 mg) was dissolved in ethanol (5 mL) and tetrahydrofuran (5 mL), 1N lithium hydroxide (1.3 mL) was added, and the mixture was stirred at room temperature for 1 hr. The solvent was evaporated under reduced pressure, and water (20 mL) was added. The mixture was neutralized with 1N hydrochloric acid under ice-cooling, and stirred for 1 hr. The resulting precipitate was collected by filtration and dried to give the title compound (284 mg, 94%). ### ORD JSON:

{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "Ethyl 3-[{[4-({1-[5-(4-methoxyphenyl)-2-methylfuran-3-yl]-3-methylbutyl}amino)phenyl]carbonyl}(methyl)amino]propanoate"}], "amount": {"mass": {"value": 660.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "ethanol hexane"}], "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "the mixture was stirred at room temperature for 1 hr"}, "conditions_are_dynamic": true}, "workups": [{"type": "WASH", "details": "eluted with ethanol-hexane (1:1, volume ratio) as mobile phase at 30\u00b0 C.", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethanol hexane"}], "reaction_role": "WORKUP"}]}, "temperature": {"setpoint": {"value": 30.0, "units": "CELSIUS"}}}, {"type": "CUSTOM", "details": "were collected"}, {"type": "CONCENTRATION", "details": "concentrated"}, {"type": "DISSOLUTION", "details": "The obtained amorphous compound (319 mg) was dissolved in ethanol (5 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "compound"}], "amount": {"mass": {"value": 319.0, "units": "MILLIGRAM"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "ADDITION", "details": "tetrahydrofuran (5 mL), 1N lithium hydroxide (1.3 mL) was added", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "tetrahydrofuran"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "lithium hydroxide"}], "amount": {"volume": {"value": 1.3, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "The solvent was evaporated under reduced pressure, and water (20 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "ADDITION", "details": "was added"}, {"type": "TEMPERATURE", "details": "cooling"}, {"type": "STIRRING", "details": "stirred for 1 hr", "duration": {"value": 1.0, "units": "HOUR"}}, {"type": "FILTRATION", "details": "The resulting precipitate was collected by filtration"}, {"type": "CUSTOM", "details": "dried"}], "outcomes": [{"reaction_time": {"value": 1.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 284.0, "units": "MILLIGRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 94.0}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: The desired compound was prepared from 6.0 g of Boc-Arg(NO2)-Gly-NH2, 40 ml of 4 N HCl-AcOEt, 3.4 ml of Et3N and 5.1 g of Boc-Pro-OSu in the same manner as in Example 26-(4). ### ORD JSON:

{"inputs": {"m0_m1_m2_m4_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "Boc-Arg(NO2)-Gly-NH2"}], "amount": {"mass": {"value": 6.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "HCl AcOEt"}], "amount": {"volume": {"value": 40.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Boc-Pro-OSu"}], "amount": {"mass": {"value": 5.1, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Et3N"}], "amount": {"volume": {"value": 3.4, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "desired compound"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: To a solution of 1-(4-(oxazol-2-yl)phenyl)piperidin-3-ol (85 mg, 0.348 mmol) in CH2Cl2 (2 mL) at 0° C. was added dropwise mesyl chloride (0.033 mL, 0.418 mmol), followed by Et3N (0.058 mL, 0.418 mmol). The reaction was stirred at 0° C. for 5 min, and then at rt for 30 min. After this time, HPLC and LC/MS showed that the desired product formed and no there was no starting material remaining. The reaction was concentrated. The residue was dissolved in EtOAc, washed with water, saturated aqueous NaHCO3 and saturated aqueous NaCl. The organic layer was dried over Na2SO4, filtered and concentrated to give the desired product 1-(4-(oxazol-2-yl)phenyl)piperidin-3-yl methanesulfonate (110 mg, 0.341 mmol, 98% yield) as an off-white foam. Anal. Calcd. for C15H18N2O4S m/z 322.3, found: 323.1 (M+H)+. ### ORD JSON:

{"inputs": {"m1_m4_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "1-(4-(oxazol-2-yl)phenyl)piperidin-3-ol"}], "amount": {"mass": {"value": 85.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "mesyl chloride"}], "amount": {"volume": {"value": 0.033, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "CH2Cl2"}], "amount": {"volume": {"value": 2.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "Et3N"}], "amount": {"volume": {"value": 0.058, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 0.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "The reaction was stirred at 0\u00b0 C. for 5 min"}, "conditions_are_dynamic": true}, "workups": [{"type": "WAIT", "details": "at rt for 30 min", "duration": {"value": 30.0, "units": "MINUTE"}, "temperature": {"control": {"type": "AMBIENT"}}}], "outcomes": [{"reaction_time": {"value": 5.0, "units": "MINUTE"}, "products": [{"identifiers": [{"type": "NAME", "value": "desired product"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: The reaction was conducted following the procedure for Example 156: step a, using. 4-(5-bromo-6-chloro-pyridine-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester (0.050 g, 0.113 mmol), (Example 2: step c), c-(tetrahydro-furan-2-yl)-methylamine (0.015 g, 0.146 mmol), diisopropylethylamine (0.073 g, 0.565 mmol), THF [0.5 mL], DMF [0.5 mL]. Chromatography of the residue (10%–35% EtOAc/Hx) yielded the title compound. ESI-MS (m/z): Calcd. for C17H19BrN2O5S4: 508.45 (M+H); found 507.1, 509.0 ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "THF"}], "amount": {"volume": {"value": 0.5, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "DMF"}], "amount": {"volume": {"value": 0.5, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(5-bromo-6-chloro-pyridine-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester"}], "amount": {"mass": {"value": 0.05, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "c-(tetrahydro-furan-2-yl)-methylamine"}], "amount": {"mass": {"value": 0.015, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m6_m0": {"components": [{"identifiers": [{"type": "NAME", "value": "EtOAc"}], "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "diisopropylethylamine"}], "amount": {"mass": {"value": 0.073, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: The title compound was prepared from (2-amino-4-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester (Example J3) (276 mg, 1.0 mmol) and (RS)-3-{3-[2-methyl-6-(tetrahydro-pyran-2-yloxymethyl)-pyridin-4-yl]-phenyl}-3-oxo-propionic acid tert-butyl ester (Example K64) (426 mg, 1.0 mmol) according to the general procedure M. Obtained as a light yellow foam (470 mg, 75%). ### ORD JSON:

{"inputs": {"m2": {"components": [{"identifiers": [{"type": "NAME", "value": "(2-amino-4-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester"}], "amount": {"mass": {"value": 276.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "(RS)-3-{3-[2-methyl-6-(tetrahydro-pyran-2-yloxymethyl)-pyridin-4-yl]-phenyl}-3-oxo-propionic acid tert-butyl ester"}], "amount": {"mass": {"value": 426.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "reaction_role": "PRODUCT"}, {"identifiers": [{"type": "NAME", "value": "foam"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 470.0, "units": "MILLIGRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 75.0}}], "texture": {"type": "FOAM", "details": "foam"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: L-alanine (1.50 g, 16.84 mmol) and 4-chlorobenzenesulfonic acid (4-CBS) (3.89 g, 20.20 mmol) were added to ethanol (15 ml), and the mixture was heated overnight at 70 EC to perform esterification. To complete the esterification reaction, the mixture was heated to 90 EC, and ethanol (200 ml) was added over 3.5 hours, while distilling away almost the same amount of ethanol. Thereafter, the solvent was evaporated under reduced pressure, and the residue was dried under reduced pressure. Ethanol (1 ml) and diethyl ether (60 ml) were added to partially crystallize an oily residue and the mixture was stirred at room temperature to give a slurry. This slurry was cooled overnight in a refrigerator and the crystals were separated and dried to give 3.52 g of L-alanine ethyl ester 4-chlorobenzenesulfonate (L-Ala-OEt 4-CBS salt) dry crystals (L-Ala-OEt 4-CBS salt content 93.6%, 10.64 mmol, yield 63.2%). ### ORD JSON:

{"inputs": {"m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "L-alanine"}], "amount": {"mass": {"value": 1.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4-chlorobenzenesulfonic acid"}], "amount": {"mass": {"value": 3.89, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"volume": {"value": 15.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "the mixture was stirred at room temperature"}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "the mixture was heated overnight at 70 EC", "duration": {"value": 8.0, "precision": 8.0, "units": "HOUR"}}, {"type": "CUSTOM", "details": "the esterification reaction"}, {"type": "ADDITION", "details": "was added over 3.5 hours", "duration": {"value": 3.5, "units": "HOUR"}}, {"type": "DISTILLATION", "details": "while distilling away almost the same amount of ethanol", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethanol"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "Thereafter, the solvent was evaporated under reduced pressure"}, {"type": "CUSTOM", "details": "the residue was dried under reduced pressure"}, {"type": "ADDITION", "details": "Ethanol (1 ml) and diethyl ether (60 ml) were added", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Ethanol"}], "amount": {"volume": {"value": 1.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "diethyl ether"}], "amount": {"volume": {"value": 60.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "to partially crystallize an oily residue"}, {"type": "CUSTOM", "details": "to give a slurry"}, {"type": "TEMPERATURE", "details": "This slurry was cooled overnight in a refrigerator", "duration": {"value": 8.0, "precision": 8.0, "units": "HOUR"}}, {"type": "CUSTOM", "details": "the crystals were separated"}, {"type": "CUSTOM", "details": "dried"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "L-alanine ethyl ester 4-chlorobenzenesulfonate"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 3.52, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 63.2}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: This compound was made in an analogous fashion to 1-ethyl-5-methyl-2-oxo-3-(3,4,5-trimethoxybenzyl)indolin-3-yl benzoate using 1-ethyl-5-methyl-2-oxoindolin-3-yl benzoate and 3,5-dimethoxy benzyl bromide (purchased from Fisher Scientific). 1H NMR δ 8.08 (d, 2H), 7.60 (t, 1H), 7.57 (t, 2H), 7.10 (d, 1H), 6.90 (s, 1H), 6.65 (d, 1H), 6.33 (s, 1H), 6.18 (s, 2H), 3.79 (m, 1H), 3.62 (s, 6H), 3.59 (m, 1H), 3.52 (d, 1H), 3.22 (d, 1H), 2.28 (s, 3H), 1.07 (t, 3H). ### ORD JSON:

{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "1-ethyl-5-methyl-2-oxo-3-(3,4,5-trimethoxybenzyl)indolin-3-yl benzoate"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "1-ethyl-5-methyl-2-oxoindolin-3-yl benzoate"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "3,5-dimethoxy benzyl bromide"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: 5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[4-(morpholin-4-ylcarbonyl)phenyl]amino}thiophene-3-carboxamide was prepared according to the general procedure in Example 1 using 2-amino-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide (0.11 g, 0.352 mmol) and 4-(4-bromobenzoyl)morpholine (0.095 g, 0.352 mmol) as the starting materials. ### ORD JSON:

{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2-amino-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]thiophene-3-carboxamide"}], "amount": {"mass": {"value": 0.11, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(4-bromobenzoyl)morpholine"}], "amount": {"mass": {"value": 0.095, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[4-(morpholin-4-ylcarbonyl)phenyl]amino}thiophene-3-carboxamide"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: To a solution of 3-benzyloxy-4-methoxyphenol (3 g) in DMSO (2 mL) was added potassium t-butoxide (1.6 g). After 30 min, 4-chloro-3,5-dimethyl-nitrobenzene (2 g) was added and the resulting solution was heated at 80° C. for 2 h. The reaction mixture was partitioned between ethyl acetate and 1 N aqueous NaOH, and the organic layer was washed with water, brine, dried over sodium sulfate and concentrated in vacuo to afford 4-(3-benzyloxy-4-methoxyphenoxy)-3,5-dimethylnitrobenzene (1.9 g) as an orange solid. ### ORD JSON:

{"inputs": {"m1_m4_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "3-benzyloxy-4-methoxyphenol"}], "amount": {"mass": {"value": 3.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "potassium t-butoxide"}], "amount": {"mass": {"value": 1.6, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DMSO"}], "amount": {"volume": {"value": 2.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "4-chloro-3,5-dimethyl-nitrobenzene"}], "amount": {"mass": {"value": 2.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 80.0, "units": "CELSIUS"}}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The reaction mixture was partitioned between ethyl acetate and 1 N aqueous NaOH", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "NaOH"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "the organic layer was washed with water, brine", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "brine"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over sodium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated in vacuo"}], "outcomes": [{"reaction_time": {"value": 30.0, "units": "MINUTE"}, "products": [{"identifiers": [{"type": "NAME", "value": "4-(3-benzyloxy-4-methoxyphenoxy)-3,5-dimethylnitrobenzene"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 1.9, "units": "GRAM"}}}], "isolated_color": "orange", "texture": {"type": "CUSTOM", "details": "solid"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: Prepared according to the procedure for 2-(2H-1,2,3-triazol-2-yl)-5-(trifluoromethyl)benzoic acid (Intermediate 37a) and 2-(1H-1,2,3-triazol-1-yl)-5-(trifluoromethyl)benzoic acid (Intermediate 37b) from 2H-1,2,3-triazole (CAS number 288-36-8; 1.0 g, 10.86 mmol) and 5-chloro-2-iodobenzoic acid (CAS number 13421-00-6; 2.00 g, 7.24 mmol). The crude solid was purified by column chromatography (silica, 0-3% methanol/DCM) to afford 5-chloro-2-(2H-1,2,3-triazol-2-yl)benzoic acid (Intermediate 38a; also commercially available CAS number 1293284-54-4). The mixed fractions were further purified by column chromatography (silica, 0-3% methanol/DCM) to afford 5-chloro-2-(1H-1,2,3-triazol-1-yl)benzoic acid (Intermediate 38b). ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Intermediate 37b"}], "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "5-chloro-2-iodobenzoic acid"}], "amount": {"mass": {"value": 2.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2-(2H-1,2,3-triazol-2-yl)-5-(trifluoromethyl)benzoic acid"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Intermediate 37a"}], "reaction_role": "REACTANT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "2H-1,2,3-triazole"}], "amount": {"mass": {"value": 1.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "2-(1H-1,2,3-triazol-1-yl)-5-(trifluoromethyl)benzoic acid"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "Prepared"}, {"type": "CUSTOM", "details": "The crude solid was purified by column chromatography (silica, 0-3% methanol/DCM)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "methanol DCM"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "Intermediate 38a"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: 4-Hydroxy-3-mercapto-6-methyl-2-pyrone (50 g., 0.317 mole) and m-fluorobenzylchloride (45.8 g., 0.317 mole) were dissolved in pyridine (250 ml.). The temperature rose from 20° to 36°C. The resulting solution was heated at 90°C. for two hours and poured over ice and 500 ml. of concd. hydrochloric acid. This mixture was extracted with methylene chloride. The extract was dried (MgSO4) and the solvent removed by evaporation. The residue was mixed with hexane, filtered and dried, yielding 44.6 g. (53 percent) of the desired product. Recrystallization from benzene gave the pure product as a white solid, m.p. 123.5°-124°C. ### ORD JSON:

{"inputs": {"m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "4-Hydroxy-3-mercapto-6-methyl-2-pyrone"}], "amount": {"mass": {"value": 50.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "m-fluorobenzylchloride"}], "amount": {"mass": {"value": 45.8, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "pyridine"}], "amount": {"volume": {"value": 250.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 90.0, "units": "CELSIUS"}}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "rose from 20\u00b0 to 36\u00b0C"}, {"type": "ADDITION", "details": "poured over ice and 500 ml"}, {"type": "EXTRACTION", "details": "This mixture was extracted with methylene chloride", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "methylene chloride"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "The extract was dried (MgSO4)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "MgSO4"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "the solvent removed by evaporation"}, {"type": "ADDITION", "details": "The residue was mixed with hexane", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "hexane"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CUSTOM", "details": "dried"}, {"type": "CUSTOM", "details": "yielding 44.6 g"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "desired product"}], "measurements": [{"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 53.0}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: In a manner analogous to the method described in example 5, rac-(4S*,5R*)-4,5-bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride was reacted with 4-piperidin-4-yl-morpholine (Aldrich) to give the title compound. HR-MS (ES, m/z) calculated for C36H40N4O3F3Cl2 [(M+H)+] 703.2424, observed 703.2419. ### ORD JSON:

{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "rac-(4S*,5R*)-4,5-bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-piperidin-4-yl-morpholine"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: Into a 10-mL sealed tube, was placed methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate (150 mg, 0.47 mmol, 1.00 equiv), 3,3-dimethylpiperidine (107 mg, 0.95 mmol, 2.00 equiv), DMSO (2 mL). The resulting solution was stirred overnight at 100° C. in an oil bath. The resulting solution was diluted with 20 mL of H2O. The resulting solids were collected by filtration. The residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:40). This resulted in 120 mg (64%) of methyl 3-(3,3-dimethylpiperidin-1-yl)-2-(4-fluorophenyl)quinoxaline-6-carboxylate as a yellow solid. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "H2O"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate"}], "amount": {"mass": {"value": 150.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "3,3-dimethylpiperidine"}], "amount": {"mass": {"value": 107.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "DMSO"}], "amount": {"volume": {"value": 2.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 100.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "The resulting solution was stirred overnight at 100\u00b0 C. in an oil bath"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "Into a 10-mL sealed tube"}, {"type": "FILTRATION", "details": "The resulting solids were collected by filtration"}, {"type": "CUSTOM", "details": "The residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:40)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate petroleum ether"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "This resulted in 120 mg (64%) of methyl 3-(3,3-dimethylpiperidin-1-yl)-2-(4-fluorophenyl)quinoxaline-6-carboxylate as a yellow solid", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl 3-(3,3-dimethylpiperidin-1-yl)-2-(4-fluorophenyl)quinoxaline-6-carboxylate"}], "amount": {"mass": {"value": 120.0, "units": "MILLIGRAM"}}, "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 8.0, "precision": 8.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "Methyl 3-(3,3-dimethylpiperidin-1-yl)-2-(4-fluorophenyl)quinoxaline-6-carboxylate"}]}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: In 30 ml of anhydrous tetrahydrofuran was suspended 5.4 g of (E)-4-methyl-6-acetoxy-4-hexen-1-yltriphenylphosphonium iodide, and to this suspension was added dropwise two molar equivalents of a n-butyllithium-hexane solution at -20° C. in a stream of nitrogen. The mixture was stirred at -20° C. for 2 hours, and to this was further added 2.5 g of (E)-6,10-dimethyl-2-oxo-5,9-undecadien-1-ol acetate (prepared in Referential example 2) in 10 ml of anhydrous tetrahydrofuran. The resulting mixture was again stirred at room temperature for 3 hours and, after addition of ice-water, extracted with ether, and from the extract was obtained an oil. The so obtained crude oil was dissolved in 25 ml of a 5% potassium hydroxide-ethanol solution under ice-cooling, and allowed to stand for 2 hours. This was, after addition of water, extracted with ether and treated in the usual way. The resultant was then chromatographed on silica gel to yield 0.95 g of the desired product. ### ORD JSON:

{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "(E)-4-methyl-6-acetoxy-4-hexen-1-yltriphenylphosphonium iodide"}], "amount": {"mass": {"value": 5.4, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "tetrahydrofuran"}], "amount": {"volume": {"value": 30.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "ice water"}], "reaction_role": "REACTANT"}]}, "m4": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "tetrahydrofuran"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m7": {"components": [{"identifiers": [{"type": "NAME", "value": "potassium hydroxide ethanol"}], "reaction_role": "SOLVENT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "(E)-6,10-dimethyl-2-oxo-5,9-undecadien-1-ol acetate"}], "amount": {"mass": {"value": 2.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": -20.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "The mixture was stirred at -20\u00b0 C. for 2 hours"}, "conditions_are_dynamic": true}, "workups": [{"type": "ADDITION", "details": "to this suspension was added dropwise two molar equivalents of a n-butyllithium-hexane solution at -20\u00b0 C. in a stream of nitrogen", "temperature": {"setpoint": {"value": -20.0, "units": "CELSIUS"}}}, {"type": "STIRRING", "details": "The resulting mixture was again stirred at room temperature for 3 hours", "duration": {"value": 3.0, "units": "HOUR"}, "temperature": {"control": {"type": "AMBIENT"}}}, {"type": "EXTRACTION", "details": "extracted with ether", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ether"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "from the extract was obtained an oil"}, {"type": "CUSTOM", "details": "The so obtained crude oil"}, {"type": "TEMPERATURE", "details": "cooling"}, {"type": "WAIT", "details": "to stand for 2 hours", "duration": {"value": 2.0, "units": "HOUR"}}, {"type": "EXTRACTION", "details": "extracted with ether", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ether"}], "reaction_role": "WORKUP"}]}}, {"type": "ADDITION", "details": "treated in the usual way"}, {"type": "CUSTOM", "details": "The resultant was then chromatographed on silica gel"}], "outcomes": [{"reaction_time": {"value": 2.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "desired product"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.95, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: A mixture of N-(4-Chlorobenzyl)-9-(4-morpholinylmethyl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxamide (1.20 g, 2.64 mmol) of preparation 6 is dissolved in dichloroethane (160 mL) followed by the addition of KHMDS (0.5 M, 5.3 mL, 2.64 mmol, 1 equiv.). Then Lawesson's reagent (2.1 g, 5.28 mmol, 2.0 equiv) and toluene (160 mL) is added and the resulting mixture is heated at reflux for 24 h. The reaction is cooled to room temperature, diluted with DCM, washed with water, brine, dried (MgSO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography (heptane/EtOAc 4/1, 1/1, 1/4, 0/1 then DCM/MeOH 19/1) and then repurified by silica gel chromatography (DCM/MeOH 11/0, 45/1, 9/1) to afford 48 mg of the title compound as a solid. ### ORD JSON:

{"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "DCM"}], "reaction_role": "SOLVENT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "N-(4-Chlorobenzyl)-9-(4-morpholinylmethyl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxamide"}], "amount": {"mass": {"value": 1.2, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "KHMDS"}], "amount": {"volume": {"value": 5.3, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Lawesson's reagent"}], "amount": {"mass": {"value": 2.1, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "toluene"}], "amount": {"volume": {"value": 160.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "dichloroethane"}], "amount": {"volume": {"value": 160.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "the resulting mixture is heated"}, {"type": "TEMPERATURE", "details": "at reflux for 24 h", "duration": {"value": 24.0, "units": "HOUR"}}, {"type": "WASH", "details": "washed with water, brine", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "brine"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried (MgSO4)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "MgSO4"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CONCENTRATION", "details": "concentrated in vacuo"}, {"type": "CUSTOM", "details": "The residue is purified by silica gel chromatography (heptane/EtOAc 4/1, 1/1, 1/4, 0/1", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "heptane EtOAc"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "DCM/MeOH 19/1) and then repurified by silica gel chromatography (DCM/MeOH 11/0, 45/1, 9/1)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "DCM MeOH"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "DCM MeOH"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 48.0, "units": "MILLIGRAM"}}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 3.9}}], "texture": {"type": "CUSTOM", "details": "solid"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: A mixture of 0.8 g of 2-amino-4-methoxy-6-methylpyrimidine, 2.8 g of the crude sulfonyl isocyanate from Example 4 and a few crystals of DABCO in 25 ml of acetonitrile was stirred at room temperature for 16 hours. A small amount of unreacted aminopyrimidine was filtered off and the filtrate concentrated in-vacuo to give a hard glass. Crystallization from methanol gave 0.9 g of N,N-diethyl-N'[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1,2-benzenedisulfonamide as a white solid, m.p. 170°-2°. ### ORD JSON:

{"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2-amino-4-methoxy-6-methylpyrimidine"}], "amount": {"mass": {"value": 0.8, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sulfonyl isocyanate"}], "amount": {"mass": {"value": 2.8, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "DABCO"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "acetonitrile"}], "amount": {"volume": {"value": 25.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "FILTRATION", "details": "A small amount of unreacted aminopyrimidine was filtered off", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "aminopyrimidine"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "the filtrate concentrated in-vacuo"}, {"type": "CUSTOM", "details": "to give a hard glass"}, {"type": "CUSTOM", "details": "Crystallization from methanol", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "methanol"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "N,N-diethyl-N'[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1,2-benzenedisulfonamide"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.9, "units": "GRAM"}}}], "isolated_color": "white", "texture": {"type": "CUSTOM", "details": "solid"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: The title compound was prepared from 4-methylthiobenzonitrile (2.50 g, 16.78 mmol) and 4-methylaniline (1.789 g, 16.78 mmol) by following the procedure described in preparation 1, (2.05 g, 47.6%, purity 79% by HPLC), mp 143-145° C. 1H-NMR (CDCl3):δ 2.33 (s, 3H), 2.52 (s, 3H), 4.75 (bs, 2H, D2O exchangeable), 6.87-6.89 (d, 2H), 7.14-7.16 (d, 2H), 7.27-7.29 (d, 2H), 7.7-7.79 (d, 2H). MS m/z: 257.1(M+). ### ORD JSON:

{"inputs": {"m0_m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-methylthiobenzonitrile"}], "amount": {"mass": {"value": 2.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4-methylaniline"}], "amount": {"mass": {"value": 1.789, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "described in preparation 1, (2.05 g, 47.6%, purity 79% by HPLC), mp 143-145\u00b0 C"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: A mixture of 3-methyl-5-(4-nitrobenzylidene)-1,3-thiazolidine-2,4-dione (1.0 g), 5% palladium carbon (1.0 g) and tetrahydrofuran (150 mL) was subjected to catalytic reduction under hydrogen pressure of 5.0 kgf·cm−2. The catalyst was removed by filtration, and the filtrate was concentrated to give 5-(4-aminobenzyl)-3-methyl-1,3-thiazolidine-2,4-dione as colorless crystals (0.71 g, yield 79%). Recrystallization thereof from ethyl acetate-hexane gave colorless prism crystals. melting point: 91-92° C. ### ORD JSON:

{"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "3-methyl-5-(4-nitrobenzylidene)-1,3-thiazolidine-2,4-dione"}], "amount": {"mass": {"value": 1.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "palladium carbon"}], "amount": {"mass": {"value": 1.0, "units": "GRAM"}}, "reaction_role": "CATALYST"}, {"identifiers": [{"type": "NAME", "value": "tetrahydrofuran"}], "amount": {"volume": {"value": 150.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The catalyst was removed by filtration"}, {"type": "CONCENTRATION", "details": "the filtrate was concentrated"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "5-(4-aminobenzyl)-3-methyl-1,3-thiazolidine-2,4-dione"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.71, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 79.0}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 79.4}}], "isolated_color": "colorless", "texture": {"type": "CRYSTAL", "details": "crystals"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: 4-(2,8-Dimethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-3-pyridin-4-yl-butyricacidmethylester (1.5 g, 3.9 mmol) was dissolved in THF (50 mL) and cooled to −78° C., tert-butyl lithium (16% in pentane) (6 mL, 15.13 mmol) was added dropwise under nitrogen. The reaction mixture was stirred at −78° C. for 90 min. After complete consumption of starting material, the reaction mixture was quenched with ammonium chloride solution and the reaction mixture was allowed to come to RT and extracted with EtOAc (3×100 mL). The combined organic layer was dried over anhydrous sodium sulfate and concentrated to obtain 1.7 g of crude 6-(2,8-dimethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-2,2-dimethyl-5-pyridin-4-yl-hexan-3-one. 1H NMR (CDCl3, freebase) δ (ppm): 8.41 (d, 2H), 7.31 (d, 1H), 7.19 (s, 1H), 7.1 (d, 1H), 6.93 (d, 2H), 4.25 (dd, 1H), 3.9 (t, 2H), 3.8 (m, 1H), 3.67 (dd, 1H), 2.87 (m, 3H), 2.71 (m, 2H), 2.51 (s, 3H), 2.42 (s, 3H), 2.1 (m, 1H), 1.21 s (9H). Separation by chiral HPLC provides enantiomers II-222a-b. ### ORD JSON:

{"inputs": {"m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(2,8-Dimethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-3-pyridin-4-yl-butyricacidmethylester"}], "amount": {"mass": {"value": 1.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "THF"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "tert-butyl lithium"}], "amount": {"volume": {"value": 6.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": -78.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "The reaction mixture was stirred at \u221278\u00b0 C. for 90 min"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "After complete consumption of starting material"}, {"type": "CUSTOM", "details": "the reaction mixture was quenched with ammonium chloride solution", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ammonium chloride"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "to come to RT", "temperature": {"control": {"type": "AMBIENT"}}}, {"type": "EXTRACTION", "details": "extracted with EtOAc (3\u00d7100 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "EtOAc"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "The combined organic layer was dried over anhydrous sodium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated"}], "outcomes": [{"reaction_time": {"value": 90.0, "units": "MINUTE"}, "products": [{"identifiers": [{"type": "NAME", "value": "6-(2,8-dimethyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-2,2-dimethyl-5-pyridin-4-yl-hexan-3-one"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 1.7, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: 1-[(5-ethyl-1,3,4-oxadiazol-2-yl)methyl]-6-phenyl-3-(piperidin-4-yl)thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione hydrochloride (200 mg; compound B29) is reacted with 4-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoic acid (168 mg; compound C10) and HBTU (191 mg) in DCM (10 ml) in the presence of DIPEA (0.29 ml) according to the procedure described in example 2 to afford the title compound after purification by twofold flash column chromatography [silica gel, eluation gradient: cyclohexane/EtOAc, 3/2 to 0/1 and DCM/MeOH, 1/0 to 1/1 (v/v)] as a solid. ### ORD JSON:

{"inputs": {"m1_m2_m3_m4_m6_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "1-[(5-ethyl-1,3,4-oxadiazol-2-yl)methyl]-6-phenyl-3-(piperidin-4-yl)thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione hydrochloride"}], "amount": {"mass": {"value": 200.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "compound B29"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoic acid"}], "amount": {"mass": {"value": 168.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "HBTU"}], "amount": {"mass": {"value": 191.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DIPEA"}], "amount": {"volume": {"value": 0.29, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DCM"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: A solution of aluminum trichloride (34.8 g, 261.4 mmol) in chloroform (120 mL) cooled to 0° C. was treated with a solution of ethyl chlorooxoacetate (18.7 mL, 167.5 mmol) in chloroform (120 mL). The mixture was stirred at 0° C. for 30 min. At this time, a solution of 2-chlorothioanisole (25.0 g, 156.5 mmol) in chloroform (120 mL) was added dropwise to the reaction mixture. It was then allowed to warm to 25° C. and stirred for an additional 3.5 h at 25° C. At this time, the reaction was quenched by the slow addition of water (500 mL) and extracted with chloroform (3×50 mL). The organics were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 80/20 hexanes/ethyl acetate) afforded (3-chloro-4-methylsulfanyl-phenyl)-oxo-acetic acid ethyl ester (31.37 g, 77%) as a yellow oil: EI-HRMS m/e calcd for C18H24Cl2N2O3 (M+) 386.1164, found 386.1154. ### ORD JSON:

{"inputs": {"m4_m7": {"components": [{"identifiers": [{"type": "NAME", "value": "2-chlorothioanisole"}], "amount": {"mass": {"value": 25.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "chloroform"}], "amount": {"volume": {"value": 120.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl chlorooxoacetate"}], "amount": {"volume": {"value": 18.7, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "chloroform"}], "amount": {"volume": {"value": 120.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "aluminum trichloride"}], "amount": {"mass": {"value": 34.8, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "chloroform"}], "amount": {"volume": {"value": 120.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 0.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "The mixture was stirred at 0\u00b0 C. for 30 min"}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "to warm to 25\u00b0 C.", "temperature": {"setpoint": {"value": 25.0, "units": "CELSIUS"}}}, {"type": "STIRRING", "details": "stirred for an additional 3.5 h at 25\u00b0 C", "duration": {"value": 3.5, "units": "HOUR"}, "temperature": {"setpoint": {"value": 25.0, "units": "CELSIUS"}}}, {"type": "CUSTOM", "details": "At this time, the reaction was quenched by the slow addition of water (500 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 500.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "EXTRACTION", "details": "extracted with chloroform (3\u00d750 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "chloroform"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "The organics were dried over sodium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CONCENTRATION", "details": "concentrated in vacuo"}], "outcomes": [{"reaction_time": {"value": 30.0, "units": "MINUTE"}, "products": [{"reaction_role": "PRODUCT"}, {"identifiers": [{"type": "NAME", "value": "(3-chloro-4-methylsulfanyl-phenyl)-oxo-acetic acid ethyl ester"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 31.37, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 77.0}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 77.5}}], "isolated_color": "yellow", "texture": {"type": "OIL", "details": "oil"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: To a solution of (1RS,2SR)-5-methyl-1-phenyl-2-(3-piperidinopropylamino)hexan-1-ol (1.66 g, 5 mmol) in toluene (25 ml) was added sodium hydride (0.14 g, 6 mmol) and the mixture was refluxed for 1 hour. To the reaction mixture was added methyl tosylate (1.12 g, 6 mmol) and the resulting mixture was refluxed for further 1 hour. After being cooled, the mixture was washed twice with water and once with brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by neutral alumina column chromatography (alumina: 40 g, eluent: chloroform) to give 1.1 g of oily matter. To a solution of the matter in acetone (20 ml) was added concentrated hydrochloric acid (0.1 ml) and the mixture was concentrated under reduced pressure. The residue was recrystallized from acetone (10 ml)-ethanol (0.2 ml) to obtain 0.45 g of the title compound as white crystals (yield: 21%). ### ORD JSON:

{"inputs": {"m6_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "amount": {"volume": {"value": 0.1, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "acetone"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1_m5_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "(1RS,2SR)-5-methyl-1-phenyl-2-(3-piperidinopropylamino)hexan-1-ol"}], "amount": {"mass": {"value": 1.66, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium hydride"}], "amount": {"mass": {"value": 0.14, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "toluene"}], "amount": {"volume": {"value": 25.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl tosylate"}], "amount": {"mass": {"value": 1.12, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "the mixture was refluxed for 1 hour", "duration": {"value": 1.0, "units": "HOUR"}}, {"type": "TEMPERATURE", "details": "the resulting mixture was refluxed for further 1 hour", "duration": {"value": 1.0, "units": "HOUR"}}, {"type": "TEMPERATURE", "details": "After being cooled"}, {"type": "WASH", "details": "the mixture was washed twice with water and once with brine", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "brine"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over anhydrous sodium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated under reduced pressure"}, {"type": "CUSTOM", "details": "The residue was purified by neutral alumina column chromatography (alumina: 40 g, eluent: chloroform)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "chloroform"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "to give 1.1 g of oily matter"}, {"type": "CONCENTRATION", "details": "the mixture was concentrated under reduced pressure"}, {"type": "CUSTOM", "details": "The residue was recrystallized from acetone (10 ml)-ethanol (0.2 ml)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "acetone"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"volume": {"value": 0.2, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.45, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 21.0}}], "isolated_color": "white", "texture": {"type": "CRYSTAL", "details": "crystals"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: A solution of trans 1-(2-hydroxymethylanilino)-2-methylaminoindane (1.16 kg; 4.3 moles) in 1,2-dibromoethane (7 l, 17.1 moles) and triethylamine (2.5 l; 34 moles) was added dropwise to stirred 1,2-dibromoethane (13 l; 31.9 moles) at ca. 100° over a period of 1.5h. This was followed by triethylamine (2.5 l; 34 moles) added dropwise over 30 min. The reaction was cooled to 50° and diethyl ether (80 l) was added with good stirring. After stirring for 1 h the precipitated triethylammonium bromide was filtered off and the resulting solution concentrated in vacuo to ca 3.5 l. Addition of ethyl acetate (2.5 l) assisted crystallisation of the required product. Filtration and trituration (pet. ether) afforded the title compound as a white crystalline solid (687 g; 54%) m.p. 166°-7°. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "1,2-dibromoethane"}], "amount": {"volume": {"value": 13.0, "units": "LITER"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "trans 1-(2-hydroxymethylanilino)-2-methylaminoindane"}], "amount": {"mass": {"value": 1.16, "units": "KILOGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1,2-dibromoethane"}], "amount": {"volume": {"value": 7.0, "units": "LITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "triethylamine"}], "amount": {"volume": {"value": 2.5, "units": "LITER"}}, "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "triethylammonium bromide"}], "reaction_role": "REACTANT"}]}, "m7": {"components": [{"identifiers": [{"type": "NAME", "value": "diethyl ether"}], "amount": {"volume": {"value": 80.0, "units": "LITER"}}, "reaction_role": "REACTANT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "triethylamine"}], "amount": {"volume": {"value": 2.5, "units": "LITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "ADDITION", "details": "added dropwise over 30 min", "duration": {"value": 30.0, "units": "MINUTE"}}, {"type": "TEMPERATURE", "details": "The reaction was cooled to 50\u00b0"}, {"type": "FILTRATION", "details": "was filtered off"}, {"type": "CONCENTRATION", "details": "the resulting solution concentrated in vacuo to ca 3.5 l"}, {"type": "ADDITION", "details": "Addition of ethyl acetate (2.5 l)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "amount": {"volume": {"value": 2.5, "units": "LITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "crystallisation of the required product", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "required product"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "Filtration and trituration (pet. ether)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "pet. ether"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 687.0, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 54.0}}], "isolated_color": "white crystalline", "texture": {"type": "CUSTOM", "details": "solid"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: A mixture of 3.55 g (0.01 mol) of 3,4-dihydro-2-(2- bromoethyl)-2,5,7,8-tetramethyl-2H-benzopyran-6-yl acetate and 2.0 g of liquid dimethylamine in 50 ml of dimethylformamide is stirred at room temperature for 40 hours. Water is added and the product is extracted with ethyl acetate and ethyl ether. The extract is washed with water, dried over anhydrous sodium sulfate, filtered and evaporated. The resulting oil crystallizes from a mixture of ethyl ether and pentane to give 2.05 g of 3,4-dihydro-2-(2-dimethylaminoethyl)-2,5,7,8-tetramethyl-2H-benzopyran-6-yl acetate as the free base. The hydrochloride salt prepared by standard methods and recrystallized from isopropanol has m.p. 263°-270° C. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Water"}], "reaction_role": "REACTANT"}]}, "m1_m2_m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "3,4-dihydro-2-(2- bromoethyl)-2,5,7,8-tetramethyl-2H-benzopyran-6-yl acetate"}], "amount": {"mass": {"value": 3.55, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "liquid"}], "amount": {"mass": {"value": 2.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dimethylamine"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dimethylformamide"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "is stirred at room temperature for 40 hours"}, "conditions_are_dynamic": true}, "workups": [{"type": "EXTRACTION", "details": "the product is extracted with ethyl acetate and ethyl ether", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "ethyl ether"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "The extract is washed with water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over anhydrous sodium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CUSTOM", "details": "evaporated"}, {"type": "CUSTOM", "details": "The resulting oil crystallizes from a mixture of ethyl ether and pentane", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl ether"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "pentane"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 40.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "3,4-dihydro-2-(2-dimethylaminoethyl)-2,5,7,8-tetramethyl-2H-benzopyran-6-yl acetate"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 2.05, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: Concentrated hydrochloric acid (2 ml) was added to N-[6-[2-(1-pyrrolidinyl)ethyl]-7,8-dihydro-2-naphthalenyl]acetamide (98.0 mg, 0.345 mmol) obtained in Reference Example 103, which was stirred at 100° C. for 16 hours. The solvent was distilled out under reduced pressure. Ethyl acetate was added to the residue, which was washed with aqueous potassium carbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then the solvent was distilled out under reduced pressure. WSC (62.5 mg, 0.326 mmol) was added to a dimethylformamide solution (1.5 ml) of the resulting oily substance (79.0 mg, 0.326 mmol), 4′-fluoro-[1,1′-biphenyl]-4-carboxylic acid (64.6 mg, 0.326 mmol) and DMAP (39.8 mg, 0.326 mmol) under ice-cooling, which was stirred at room temperature for 1 day. Ethyl acetate was added to the reaction mixture, which was washed with aqueous potassium carbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent was distilled out under reduced pressure. The resulting residue was purified by aluminum column chromatography (development solvent; ethyl acetate), powdered with ethyl acetate-isopropyl ether (1:5), to give the titled compound (75.1 mg). ### ORD JSON:

{"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "Ethyl acetate"}], "reaction_role": "SOLVENT"}]}, "m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "amount": {"volume": {"value": 2.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "N-[6-[2-(1-pyrrolidinyl)ethyl]-7,8-dihydro-2-naphthalenyl]acetamide"}], "amount": {"mass": {"value": 98.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m3_m7_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "WSC"}], "amount": {"mass": {"value": 62.5, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4\u2032-fluoro-[1,1\u2032-biphenyl]-4-carboxylic acid"}], "amount": {"mass": {"value": 64.6, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DMAP"}], "amount": {"mass": {"value": 39.8, "units": "MILLIGRAM"}}, "reaction_role": "CATALYST"}, {"identifiers": [{"type": "NAME", "value": "dimethylformamide"}], "amount": {"volume": {"value": 1.5, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 100.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "was stirred at 100\u00b0 C. for 16 hours"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "obtained in Reference Example 103, which"}, {"type": "DISTILLATION", "details": "The solvent was distilled out under reduced pressure"}, {"type": "ADDITION", "details": "Ethyl acetate was added to the residue, which", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Ethyl acetate"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "was washed with aqueous potassium carbonate solution and saturated aqueous sodium chloride solution", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "potassium carbonate"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "sodium chloride"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over anhydrous sodium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "DISTILLATION", "details": "the solvent was distilled out under reduced pressure"}, {"type": "TEMPERATURE", "details": "cooling"}, {"type": "STIRRING", "details": "which was stirred at room temperature for 1 day", "duration": {"value": 1.0, "units": "DAY"}, "temperature": {"control": {"type": "AMBIENT"}}}, {"type": "WASH", "details": "was washed with aqueous potassium carbonate solution and saturated aqueous sodium chloride solution", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "potassium carbonate"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "sodium chloride"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over anhydrous sodium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "DISTILLATION", "details": "the solvent was distilled out under reduced pressure"}, {"type": "CUSTOM", "details": "The resulting residue was purified by aluminum column chromatography (development solvent; ethyl acetate)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "aluminum"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 16.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "titled compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 75.1, "units": "MILLIGRAM"}}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: A solution of 1-benzyl-4-(3-methylphenylamino)-isonipecotamide (4.5 g, 13.9 mmol) and potassium hydroxide (3. g, 53.5 mmol) in ethylene glycol (35 mL) was heated under reflux. The resulting mixture was diluted with water and neutralized with acetic acid. The white solid precipitated was filtered, washed with chloroform to provide 1-benzyl-4-(3-methylphenylamino)piperidine-4-carboxylic acid. ### ORD JSON:

{"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "1-benzyl-4-(3-methylphenylamino)-isonipecotamide"}], "amount": {"mass": {"value": 4.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "potassium hydroxide"}], "amount": {"moles": {"value": 53.5, "units": "MILLIMOLE"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethylene glycol"}], "amount": {"volume": {"value": 35.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "acetic acid"}], "reaction_role": "SOLVENT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "under reflux"}, {"type": "CUSTOM", "details": "The white solid precipitated"}, {"type": "FILTRATION", "details": "was filtered"}, {"type": "WASH", "details": "washed with chloroform", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "chloroform"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "1-benzyl-4-(3-methylphenylamino)piperidine-4-carboxylic acid"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: 2-chlorosulphenylbenzoyl chloride (10.35 parts; 0.005M) was slowly added to a stirred solution of 2-ethylhexylamine (29.8 parts; 0.23M;) in diethylether (150 ml) at below 5° C. The reactants were then stirred overnight, allowing the temperature to rise to 18° to 20° C. Iced water was then added and the mix made just acid to Congo red by dropwise addition of of concentrated hydrochloric acid, keeping the temperature below 5° C. The ether layer was then separated and dried over magnesium sulphate. The solution was then filtered and the ether evaporated leaving a syrupy oil. This was boiled with petroleum ether (bp 60°-80° C.), the ether layer decanted from some tarry material and then evaporated to dryness leaving a dark yellow oil. This oil was purified by high vacuum distillation in a Kugelrohr and 8.4 parts pale yellow liquid obtained (Yield 64% theory). ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Congo red"}], "reaction_role": "REACTANT"}]}, "m7": {"components": [{"identifiers": [{"type": "NAME", "value": "petroleum ether"}], "reaction_role": "SOLVENT"}]}, "m1_m2_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "2-chlorosulphenylbenzoyl chloride"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-ethylhexylamine"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "diethylether"}], "amount": {"volume": {"value": 150.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "REACTANT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "The reactants were then stirred overnight"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "to rise to 18\u00b0 to 20\u00b0 C"}, {"type": "ADDITION", "details": "was then added"}, {"type": "CUSTOM", "details": "the temperature below 5\u00b0 C"}, {"type": "CUSTOM", "details": "The ether layer was then separated", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ether"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over magnesium sulphate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "magnesium sulphate"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "The solution was then filtered"}, {"type": "CUSTOM", "details": "the ether evaporated", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ether"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "leaving a syrupy oil"}, {"type": "CUSTOM", "details": "the ether layer decanted from some tarry material", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ether"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "evaporated to dryness"}, {"type": "CUSTOM", "details": "leaving a dark yellow oil"}, {"type": "DISTILLATION", "details": "This oil was purified by high vacuum distillation in a Kugelrohr and 8.4 parts pale yellow liquid"}, {"type": "CUSTOM", "details": "obtained (Yield 64% theory)"}], "outcomes": [{"reaction_time": {"value": 8.0, "precision": 8.0, "units": "HOUR"}, "products": [{"measurements": [{"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 64.0}}]}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: To a reaction apparatus equipped with a thermometer, reflux condenser and stirrer, 60 g (0.131 mol) of 3,3'-dinitro-4,4'-diphenoxybenzophenone, 150 g of methyl cellosolve and 3.0 g of 5%-Pd/C (50% moisture content) were charged and reacted in a hydrogen atmosphere at 70°~80° C. for 4 hours. After finishing the reaction, the catalyst was filtered and the filtrate was concentrated under reduced pressure to obtain 45 g (86% yield) of 3,3'-diamino-4,4'-diphenoxybenzophenone as light yellow crystals. ### ORD JSON:

{"inputs": {"m1_m4_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "3,3'-dinitro-4,4'-diphenoxybenzophenone"}], "amount": {"mass": {"value": 60.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Pd/C"}], "reaction_role": "CATALYST"}, {"identifiers": [{"type": "NAME", "value": "methyl cellosolve"}], "amount": {"mass": {"value": 150.0, "units": "GRAM"}}, "reaction_role": "SOLVENT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrogen"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "To a reaction apparatus equipped with a thermometer"}, {"type": "TEMPERATURE", "details": "reflux condenser and stirrer"}, {"type": "CUSTOM", "details": "the reaction"}, {"type": "FILTRATION", "details": "the catalyst was filtered"}, {"type": "CONCENTRATION", "details": "the filtrate was concentrated under reduced pressure"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "3,3'-diamino-4,4'-diphenoxybenzophenone"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 45.0, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 86.0}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 86.6}}], "isolated_color": "light yellow", "texture": {"type": "CRYSTAL", "details": "crystals"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: By reacting 3-nitrophenylhydrazine as in the same manner as (1), 430 g of 2-(3-nitrophenyl)-1-formylhydrazine was obtained. Melting point: 168° to 169° C. ### ORD JSON:

{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "3-nitrophenylhydrazine"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "( 1 )"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "2-(3-nitrophenyl)-1-formylhydrazine"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 430.0, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: from 3-(1,2,3,5,8,8a-hexahydro-7-indolizinyl)-1H-5-Azaindole (10 mg, 0.0418 mmol), benzenesulfonyl chloride (20 mg, 0.113 mmol) and 1M NaN(TMS)2 (100 μL, 0.10 mmol) in THF (0.5 mL) at RT. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "THF"}], "amount": {"volume": {"value": 0.5, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "3-(1,2,3,5,8,8a-hexahydro-7-indolizinyl)-1H-5-Azaindole"}], "amount": {"mass": {"value": 10.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "benzenesulfonyl chloride"}], "amount": {"mass": {"value": 20.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "NaN(TMS)2"}], "amount": {"volume": {"value": 100.0, "units": "MICROLITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "at RT", "temperature": {"control": {"type": "AMBIENT"}}}], "outcomes": [{"products": [{}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: Prepared from 3-t-butoxycarbonylamino-3-methylbutanoic acid (Example 31, Step E) and 3(R)-amino-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (Example 1, Step B) by the procedure described in Example 1, Step F. 1H NMR (200 MHz, CDCl3): 1.37 (s,6H), 1.44 (s,9H), 1.95 (m,1H), 2.46 (d,15 Hz,1H), 2.59 (d,15 Hz,1H), 2.6-3.0, (m,3H), 4.53 (m,1H), 5.30 (br s,1H), 6.72 (d,7 Hz,1H), 6.98 (d,8 Hz,1H), 7.1-7.3 (m,3H), 7.82 (br s,1H). FAB-MS: calculated for C20H29N3O4 375; found 376 (M+H,70%). ### ORD JSON:

{"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "3-t-butoxycarbonylamino-3-methylbutanoic acid"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "3(R)-amino-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "C20H29N3O4"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: At ice-bath temperature, lithium aluminium hydride (1.6 g, 42.16 mmol) was added in portions to a stirring mixture of (S)-2-benzyl piperazine-3,6-dione (3.0 g, 14.70 mmol) and tetrahydrofuran (80 ml). After 30 min at ice-bath temperature, the mixture was refluxed for 4 h with stirring. The reaction was quenched by the portionwise addition of sodium sulfate decahydrate and some methanol until hydrogen evolution ceased. It was filtered and the solids were washed several times with dichloromethane. The combined filtrates were evaporated to leave a white solid. MS (m/z): 177.1 (M+H)+; C11H16N2 requir. 176.3. ### ORD JSON:

{"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "lithium aluminium hydride"}], "amount": {"mass": {"value": 1.6, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "(S)-2-benzyl piperazine-3,6-dione"}], "amount": {"mass": {"value": 3.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tetrahydrofuran"}], "amount": {"volume": {"value": 80.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "with stirring"}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "the mixture was refluxed for 4 h", "duration": {"value": 4.0, "units": "HOUR"}}, {"type": "CUSTOM", "details": "The reaction was quenched by the portionwise addition of sodium sulfate decahydrate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium sulfate decahydrate"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "It was filtered"}, {"type": "WASH", "details": "the solids were washed several times with dichloromethane", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "The combined filtrates were evaporated"}, {"type": "CUSTOM", "details": "to leave a white solid"}], "outcomes": [{"reaction_time": {"value": 30.0, "units": "MINUTE"}, "products": [{}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: To a solution (4-bromo-phenyl)-pyrrolidin-3-yl-methanone (2.24 g, 8.81 mmol) in methanol (44 mL), add acetic acid (1.01 mL, 17.6 mmol) and formaldehyde (2.15 g, 26.4 mmol, 37% aqueous solution). After 15 min, add sodium triacetoxyborohydride (5.60 g, 26.4 mmol) and allow the mixture to stir at RT for one hour. Concentrate the reaction mixture. Add water and adjust the solution to pH=10 with 2 N NaOH. Extract the aqueous with ethylacetate. Dry the combined organic layers over Na2SO4, filter, and concentrate. Purify the crude material by flash chromatography, eluting with 5-10% MeOH (2N NH3)/CH2Cl2 to give 1.61 g (68%) of the title compound. LC-MS/ES m/z (79Br) 268.0 [M+H]+. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium triacetoxyborohydride"}], "amount": {"mass": {"value": 5.6, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m1_m5_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "(4-bromo-phenyl)-pyrrolidin-3-yl-methanone"}], "amount": {"mass": {"value": 2.24, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "acetic acid"}], "amount": {"volume": {"value": 1.01, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "formaldehyde"}], "amount": {"mass": {"value": 2.15, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methanol"}], "amount": {"volume": {"value": 44.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "to stir at RT for one hour"}, "conditions_are_dynamic": true}, "workups": [{"type": "CONCENTRATION", "details": "Concentrate the reaction mixture"}, {"type": "EXTRACTION", "details": "Extract the aqueous with ethylacetate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethylacetate"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "Dry the combined organic layers over Na2SO4", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Na2SO4"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filter"}, {"type": "CONCENTRATION", "details": "concentrate"}, {"type": "CUSTOM", "details": "Purify the crude material by flash chromatography", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "crude material"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "eluting with 5-10% MeOH (2N NH3)/CH2Cl2", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "MeOH"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "CH2Cl2"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 15.0, "units": "MINUTE"}, "products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 1.61, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 68.0}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 68.2}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: An aqueous solution of 8.06 g 50 wt % H3PO2 reagent was combined with 6.00 g distilled water to form a clear, colorless solution in a 250 ml Pyrex beaker on a hotplate/stirrer. To this solution was added 19.23 g Ca(NO3)2.4H2O. The molar ratio of Ca/phosphate in this sample was 4/3 and the equivalent solids [as octacalcium phosphate, Ca8H2(PO4)6-5H2O] was 30.0 wt %. Endothermic dissolution of the calcium nitrate tetrahydrate proceeded under ambient conditions, eventually forming a homogeneous solution once the sample warmed to room temperature. Warming of the solution above 25° C. initiated a vigorous exothermic reaction as described in Example 1. After approximately three minutes, the reaction was essentially complete leaving a moist, white, pasty solid. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "octacalcium phosphate"}], "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "calcium nitrate tetrahydrate"}], "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "H3PO2"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Ca(NO3)2.4H2O"}], "amount": {"mass": {"value": 19.23, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "Ca8H2(PO4)6-5H2O"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "Ca phosphate"}], "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "conditions_are_dynamic": true}, "workups": [{"type": "DISTILLATION", "details": "distilled water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "to form a clear, colorless solution in a 250 ml Pyrex beaker on a hotplate/stirrer"}, {"type": "CUSTOM", "details": "eventually forming a homogeneous solution once the sample"}, {"type": "TEMPERATURE", "details": "Warming of the solution above 25\u00b0 C."}, {"type": "CUSTOM", "details": "a vigorous exothermic reaction"}, {"type": "CUSTOM", "details": "the reaction was essentially complete leaving a moist, white, pasty solid"}], "outcomes": [{"reaction_time": {"value": 3.0, "units": "MINUTE"}, "products": [{"identifiers": [{"type": "NAME", "value": "Calcium Phosphate"}]}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: To a solution containing 0.05 g (0.18 mmol) of N2-mesityl-1-methyl-1H-benzimidazole-2,7-diamine in methanol (5 ml) was added 0.03 ml (0.54 mmol) of propionaldehyde, 0.03 g (0.54 mmol) of NaBH3CN and 0.1 ml of acetic acid. The mixture was stirred overnight then diluted with ethyl acetate and washed with water. The organic phase was dried over magnesium sulfate. Filtration, removal of solvent and purification of the residue via Biotage chromatography eluting with 5% methanol/dichloromethane gave 0.04 g (70%) of product. ### ORD JSON:

{"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "SOLVENT"}]}, "m1_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "N2-mesityl-1-methyl-1H-benzimidazole-2,7-diamine"}], "amount": {"mass": {"value": 0.05, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methanol"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "propionaldehyde"}], "amount": {"volume": {"value": 0.03, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "NaBH3CN"}], "amount": {"mass": {"value": 0.03, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "acetic acid"}], "amount": {"volume": {"value": 0.1, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "The mixture was stirred overnight"}, "conditions_are_dynamic": true}, "workups": [{"type": "WASH", "details": "washed with water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "The organic phase was dried over magnesium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "magnesium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "Filtration, removal of solvent and purification of the residue via Biotage chromatography"}, {"type": "WASH", "details": "eluting with 5% methanol/dichloromethane", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "methanol dichloromethane"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 8.0, "precision": 8.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "product"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.04, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 70.0}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: A mixture of 5-phenylcyclohexane-1,3-dione (4.0 g), 4-aminobutan-2-ol (2.5 g), molecular sieves 4A (24 g) and tetrahydrofuran (60 ml) was refluxed for 13 hours and cooled, and insoluble materials were filtered off. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in dimethylformamide (100 ml). To the solution were 2-bromomesitylene(4.2 g), tetrakistriphenylphosphine palladium (0.6 g) and potassium carbonate (5.9 g), and the mixture was stirred at 150° C. for 5 hours and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, and the solution was washed with sodium hydrogen carbonate solution, water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (EtOAc/hexane) to give colorless crystals of 3-ethyl-6-phenyl-4,5,6,7-tetrahydroindol-4-one (2.6 g). ### ORD JSON:

{"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "5-phenylcyclohexane-1,3-dione"}], "amount": {"mass": {"value": 4.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4-aminobutan-2-ol"}], "amount": {"mass": {"value": 2.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4A"}], "amount": {"mass": {"value": 24.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tetrahydrofuran"}], "amount": {"volume": {"value": 60.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 150.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "the mixture was stirred at 150\u00b0 C. for 5 hours"}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "was refluxed for 13 hours", "duration": {"value": 13.0, "units": "HOUR"}}, {"type": "TEMPERATURE", "details": "cooled"}, {"type": "FILTRATION", "details": "insoluble materials were filtered off"}, {"type": "CUSTOM", "details": "Under reduced pressure, the solvent was evaporated"}, {"type": "DISSOLUTION", "details": "the residue was dissolved in dimethylformamide (100 ml)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "dimethylformamide"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated under reduced pressure"}, {"type": "DISSOLUTION", "details": "The residue was dissolved in ethyl acetate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "the solution was washed with sodium hydrogen carbonate solution, water and saturated brine", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium hydrogen carbonate"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "brine"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried with magnesium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "magnesium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated under reduced pressure"}, {"type": "CUSTOM", "details": "The residue was purified with silica gel column chromatography (EtOAc/hexane)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "EtOAc hexane"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 5.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "3-ethyl-6-phenyl-4,5,6,7-tetrahydroindol-4-one"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 2.6, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: N-(5-Acetylamino-2-methyl-phenyl)-2,2,2-trifluoro-acetamide (2.93 g, 11.24 mmol) was taken up in methanol (50 mL) and sodium carbonate (5.96 g, 56.20 mmol) was added. The reaction was stirred at room temp for 12 h. The reaction mixture was into water and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent removed under reduced pressure. The product was utilized without further purification. Yield 1.60 g. 1H NMR (CDCl3, 300 MHz): 82.16 (s, 3H). 2.31 (s, 3H), 7.18 (d, J=9 Hz, 1H), 7.32 (d, J=9 Hz, 1H), 7.64 (s, 1H). ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "methanol"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "N-(5-Acetylamino-2-methyl-phenyl)-2,2,2-trifluoro-acetamide"}], "amount": {"mass": {"value": 2.93, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium carbonate"}], "amount": {"mass": {"value": 5.96, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "The reaction was stirred at room temp for 12 h"}, "conditions_are_dynamic": true}, "workups": [{"type": "EXTRACTION", "details": "the aqueous layer was extracted three times with ethyl acetate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "The combined organic layers were washed with brine", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "brine"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over anhydrous magnesium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "magnesium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "The solution was filtered"}, {"type": "CUSTOM", "details": "the solvent removed under reduced pressure"}, {"type": "CUSTOM", "details": "The product was utilized without further purification"}], "outcomes": [{"reaction_time": {"value": 12.0, "units": "HOUR"}, "products": [{}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: To a solution of (Z)-2-((2-(tert-butoxy)-2-oxoethoxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetic acid (108 mg, 0.269 mmol) in DCM (2.7 mL) at 0° C. was added DIPEA (141 μL, 0.808 mmol) followed by HATU (113 mg, 0.296 mmol). To the resulting solution, after 20 min, was added a solution of (3S,4R)-4-((1H-1,2,4-triazol-1-yl)methyl)-3-aminoazetidin-2-one (50 mg, 0.299 mmol) in DCM. After 1 h of stirring it was diluted with EtOAc, washed with water, brine, dried over Na2SO4 and concentrated in vacuo. The crude residue was purified via silica gel chromatography (Acetone-DCM) to afford the title compound (106 mg, 72%). LCMS: R=0.78 min, m/z=551.2 (M+1) Method 2m_acidic. ### ORD JSON:

{"inputs": {"m1_m5_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "(Z)-2-((2-(tert-butoxy)-2-oxoethoxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetic acid"}], "amount": {"mass": {"value": 108.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DIPEA"}], "amount": {"volume": {"value": 141.0, "units": "MICROLITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DCM"}], "amount": {"volume": {"value": 2.7, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m7": {"components": [{"identifiers": [{"type": "NAME", "value": "EtOAc"}], "reaction_role": "SOLVENT"}]}, "m4_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "(3S,4R)-4-((1H-1,2,4-triazol-1-yl)methyl)-3-aminoazetidin-2-one"}], "amount": {"mass": {"value": 50.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DCM"}], "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "HATU"}], "amount": {"mass": {"value": 113.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "After 1 h of stirring it"}, "conditions_are_dynamic": true}, "workups": [{"type": "WASH", "details": "washed with water, brine", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "brine"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over Na2SO4", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Na2SO4"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated in vacuo"}, {"type": "CUSTOM", "details": "The crude residue was purified via silica gel chromatography (Acetone-DCM)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "crude residue"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "Acetone DCM"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 20.0, "units": "MINUTE"}, "products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 106.0, "units": "MILLIGRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 72.0}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: (R)-Mandelic acid (20 g, 130 mmol) was dissolved in anhydrous pentane (200 mL, 1.7 mol). Pivaldehyde (13.6 g, 153 mmol) was added followed by trifluoromethanesulfonic acid (488 μL, 5.4 mmol). The reaction was allowed to reflux at 36° C. under nitrogen. After 5.5 hours, the mixture was allowed to cool to room temperature before stirring with 200 mL of an 8 wt % NaHCO3 solution for 10 minutes. Excess pentane was removed by rotary evaporation. The solids were collected by filtration and rinsed (100 mL water) while under vacuum filtration. The solids were dried overnight under high vacuum to yield 23.8 grams of intermediate (1a) as a white solid (88% purity). ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "NaHCO3"}], "reaction_role": "REACTANT"}]}, "m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "(R)-Mandelic acid"}], "amount": {"mass": {"value": 20.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "pentane"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "trifluoromethanesulfonic acid"}], "amount": {"volume": {"value": 488.0, "units": "MICROLITER"}}, "reaction_role": "CATALYST"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "Pivaldehyde"}], "amount": {"mass": {"value": 13.6, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 36.0, "units": "CELSIUS"}}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "to cool to room temperature", "temperature": {"control": {"type": "AMBIENT"}}}, {"type": "CUSTOM", "details": "Excess pentane was removed by rotary evaporation", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "pentane"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "The solids were collected by filtration"}, {"type": "WASH", "details": "rinsed (100 mL water)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "while under vacuum filtration"}, {"type": "CUSTOM", "details": "The solids were dried overnight under high vacuum", "duration": {"value": 8.0, "precision": 8.0, "units": "HOUR"}}], "outcomes": [{"reaction_time": {"value": 5.5, "units": "HOUR"}, "products": [{"measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 23.8, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 88.0}}], "isolated_color": "white", "texture": {"type": "CUSTOM", "details": "solid"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: To a mixture of 7-(2-bromothiophen-3-yl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (0.245 g) and 1-amino-3-hydroxyguanidine p-toluenesulfonate (262 mg) were added ethanol (3 ml) and concentrated hydrochloric acid (0.1 ml), and the mixture was stirred at 90° C. for 2 hours. Under reduced pressure, the solvent was evaporated, and to the residue was added 0.2N sodium hydroxide solution (20 ml). The mixture was extracted with a mixture of ethyl acetate (20 ml) and tetrahydrofuran (20 ml). The organic layer was washed with 0.2N sodium hydroxide solution (20 ml) and water, to which was added 2N hydrochloric acid (0.8 ml). The mixture was concentrated, and to the residue was added ethanol (3 ml). The mixture was stirred at 90° C. for 3 hours and cooled, and precipitated crystals were filtered, washed with ethanol and dried to give 7-(2-bromothiophen-3-yl)-5-(1-hydroxyguanidin-3-yl)imino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound 125) (0.215 g) as pale yellow crystals. ### ORD JSON:

{"inputs": {"m4_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "amount": {"volume": {"value": 0.1, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"volume": {"value": 3.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "7-(2-bromothiophen-3-yl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one"}], "amount": {"mass": {"value": 0.245, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1-amino-3-hydroxyguanidine p-toluenesulfonate"}], "amount": {"mass": {"value": 262.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 90.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "the mixture was stirred at 90\u00b0 C. for 2 hours"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "Under reduced pressure, the solvent was evaporated"}, {"type": "ADDITION", "details": "to the residue was added 0.2N sodium hydroxide solution (20 ml)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium hydroxide"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "EXTRACTION", "details": "The mixture was extracted with a mixture of ethyl acetate (20 ml) and tetrahydrofuran (20 ml)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "tetrahydrofuran"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "The organic layer was washed with 0.2N sodium hydroxide solution (20 ml) and water, to which", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium hydroxide"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "ADDITION", "details": "was added 2N hydrochloric acid (0.8 ml)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "amount": {"volume": {"value": 0.8, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "The mixture was concentrated"}, {"type": "ADDITION", "details": "to the residue was added ethanol (3 ml)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"volume": {"value": 3.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "STIRRING", "details": "The mixture was stirred at 90\u00b0 C. for 3 hours", "duration": {"value": 3.0, "units": "HOUR"}, "temperature": {"setpoint": {"value": 90.0, "units": "CELSIUS"}}}, {"type": "TEMPERATURE", "details": "cooled"}, {"type": "CUSTOM", "details": "precipitated crystals"}, {"type": "FILTRATION", "details": "were filtered"}, {"type": "WASH", "details": "washed with ethanol", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethanol"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "dried"}], "outcomes": [{"reaction_time": {"value": 2.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "7-(2-bromothiophen-3-yl)-5-(1-hydroxyguanidin-3-yl)imino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.215, "units": "GRAM"}}}], "isolated_color": "pale yellow", "texture": {"type": "CRYSTAL", "details": "crystals"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: To a solution of methyl 5-acetyl-2-(2-fluorophenylamino)-3,4-difluorobenzoate (500 mg, 1.55 mmol, from step D in example 3) in DMF (10 ml) was added hydrazine (0.06 mL, 185 mmol). After stirring at room temperature for 16 h, the reaction was quenched with NH4Cl solution and extracted with EtOAc. The organic layer was dried (MgSO4) and concentrated under reduced pressure to afford 740 mg (75%) of the title compound. ### ORD JSON:

{"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl 5-acetyl-2-(2-fluorophenylamino)-3,4-difluorobenzoate"}], "amount": {"mass": {"value": 500.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "hydrazine"}], "amount": {"volume": {"value": 0.06, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DMF"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "After stirring at room temperature for 16 h"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "the reaction was quenched with NH4Cl solution", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "NH4Cl"}], "reaction_role": "WORKUP"}]}}, {"type": "EXTRACTION", "details": "extracted with EtOAc", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "EtOAc"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "The organic layer was dried (MgSO4)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "MgSO4"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated under reduced pressure"}], "outcomes": [{"reaction_time": {"value": 16.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 740.0, "units": "MILLIGRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 75.0}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: Into a 100-mL 3-necked round-bottom flask purged and maintained under an inert atmosphere of nitrogen, was placed tert-butyl (2R)-2-([4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl]methyl)pyrrolidine-1-carboxylate (300 mg, 0.68 mmol, 1.00 equiv), prepared as described in Example 1 except in the Mitsunobu reaction using (R)-tert-butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate instead of (S)-tert-butyl 3-hydroxypiperidine-1-carboxylate, 2-[4-(3-fluorophenoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (254 mg, 0.81 mmol, 1.20 equiv), tetrakis(triphenylphosphane) palladium (47 mg, 0.04 mmol, 0.06 equiv), ethylene glycol dimethyl ether (50 mL), sodium carbonate (180 mg, 1.70 mmol, 2.50 equiv), water (10 mL). The resulting solution was stirred for 12 h at 80° C. in an oil bath. The resulting mixture was concentrated under vacuum. The resulting solution was extracted with dichloromethane and the organic layers combined, dried and concentrated under vacuum. The residue was loaded on a silica gel column and eluted with dichloromethane/methanol (50/1) to give 0.27 g (79%) of tert-butyl (2R)-2-([4-amino-3-[4-(3-fluorophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]methyl)pyrrolidine-1-carboxylate as a brown solid. ### ORD JSON:

{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "tert-butyl (2R)-2-([4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl]methyl)pyrrolidine-1-carboxylate"}], "amount": {"mass": {"value": 300.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "tetrakis(triphenylphosphane) palladium"}], "amount": {"mass": {"value": 47.0, "units": "MILLIGRAM"}}, "reaction_role": "CATALYST"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "2-[4-(3-fluorophenoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane"}], "amount": {"mass": {"value": 254.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m4": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium carbonate"}], "amount": {"mass": {"value": 180.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m7": {"components": [{"identifiers": [{"type": "NAME", "value": "ethylene glycol dimethyl ether"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "(R)-tert-butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate"}], "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 80.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "The resulting solution was stirred for 12 h at 80\u00b0 C. in an oil bath"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "Into a 100-mL 3-necked round-bottom flask purged"}, {"type": "TEMPERATURE", "details": "maintained under an inert atmosphere of nitrogen"}, {"type": "CUSTOM", "details": "prepared"}, {"type": "CUSTOM", "details": "as described in Example 1 except in the Mitsunobu reaction"}, {"type": "CONCENTRATION", "details": "The resulting mixture was concentrated under vacuum"}, {"type": "EXTRACTION", "details": "The resulting solution was extracted with dichloromethane", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "dried"}, {"type": "CONCENTRATION", "details": "concentrated under vacuum"}, {"type": "WASH", "details": "eluted with dichloromethane/methanol (50/1)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "dichloromethane methanol"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 12.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "tert-butyl (2R)-2-([4-amino-3-[4-(3-fluorophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-1-yl]methyl)pyrrolidine-1-carboxylate"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.27, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 79.0}}], "isolated_color": "brown", "texture": {"type": "CUSTOM", "details": "solid"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: 25 g of epoxy-cyclododecane and 1 g of lithium chloride were dissolved in 20 g of N,N'-dimethyl ethylene urea and the solvent was stirred at 200° C. for 6 hours. The reaction mixture was analyzed to have a 94% yield of cyclododecanone. ### ORD JSON:

{"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "epoxy-cyclododecane"}], "amount": {"mass": {"value": 25.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "lithium chloride"}], "amount": {"mass": {"value": 1.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "N,N'-dimethyl ethylene urea"}], "amount": {"mass": {"value": 20.0, "units": "GRAM"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 200.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "the solvent was stirred at 200\u00b0 C. for 6 hours"}, "conditions_are_dynamic": true}, "outcomes": [{"reaction_time": {"value": 6.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "cyclododecanone"}], "measurements": [{"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 94.0}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: 6-Methoxy-4-(3-methylamino-1-phenyl-propyl)-1H-indole-3-carbonitrile CXXXII (90 mg) was prepared from 4-(3-hydroxy-1-phenyl-propyl)-6-methoxy-1H-indole-3-carbonitrile using the procedure described above for preparation of 5-(3-Methylamino-1-pheny-propyl)-1H-indole-3-carbonitrile LXVI. MS (M+H)=320. ### ORD JSON:

{"inputs": {"m2": {"components": [{"identifiers": [{"type": "NAME", "value": "5-(3-Methylamino-1-pheny-propyl)-1H-indole-3-carbonitrile"}], "reaction_role": "REACTANT"}]}, "m0_m1": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(3-hydroxy-1-phenyl-propyl)-6-methoxy-1H-indole-3-carbonitrile"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "6-Methoxy-4-(3-methylamino-1-phenyl-propyl)-1H-indole-3-carbonitrile"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: (2E)-5-(tert-Butoxycarbonylamino)-5-methylhex-2-enoic acid (81 mg, 0.33 mmol) was dissolved in N,N-dimethylformamide (2 ml) and dichloromethane (2 ml). 1-Hydroxy-7-azabenzotriazole (45 mg, 0.33 mmol) was added. The solution was cooled to 0° C. N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (69 mg, 0.36 mmol) was added. A solution of 1,1-dimethyl-2-((2R)-2-(N-methyl-N-((2R)-2-methylamino-3-(2-naphthyl)propionyl)amino)-3-phenylpropionylamino)ethyl acetate (152 mg, 0.30 mmol) in dichloromethane (2 ml) and ethyldiisopropylamine (0.05 ml, 0.30 mmol) were added successively. The solution was stirred for 16 h, while warming up to room temperature. It was diluted with ethyl acetate (150 ml), washed with 1N hydrochloric acid (100 ml) and saturated sodium hydrogen carbonate solution, and dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (40 g), using ethyl acetate/heptane (first 1:1 (250 ml), then 2:1) to give 221 mg of 2-((2R)-2-(N-((2R)-2-(N-((2E)-5-(tert-butoxycarbonylamino)-5-methylhex-2-enoyl)-N-methylamino)-3-(2-naphthyl)propionyl)-N-methylamino)-3-phenylpropionylamino)-1,1-dimethylethyl acetate. ### ORD JSON:

{"inputs": {"m7": {"components": [{"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 2.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m4_m8_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "1,1-dimethyl-2-((2R)-2-(N-methyl-N-((2R)-2-methylamino-3-(2-naphthyl)propionyl)amino)-3-phenylpropionylamino)ethyl acetate"}], "amount": {"mass": {"value": 152.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethyldiisopropylamine"}], "amount": {"volume": {"value": 0.05, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 2.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "(2E)-5-(tert-Butoxycarbonylamino)-5-methylhex-2-enoic acid"}], "amount": {"mass": {"value": 81.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "N,N-dimethylformamide"}], "amount": {"volume": {"value": 2.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "1-Hydroxy-7-azabenzotriazole"}], "amount": {"mass": {"value": 45.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m9": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "amount": {"volume": {"value": 150.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride"}], "amount": {"mass": {"value": 69.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 0.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "The solution was stirred for 16 h"}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "while warming up to room temperature", "temperature": {"control": {"type": "AMBIENT"}}}, {"type": "WASH", "details": "washed with 1N hydrochloric acid (100 ml) and saturated sodium hydrogen carbonate solution", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "sodium hydrogen carbonate"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over magnesium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "magnesium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "The solvent was removed in vacuo"}, {"type": "CUSTOM", "details": "The crude product was purified by flash chromatography on silica (40 g)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "crude product"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 16.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "2-((2R)-2-(N-((2R)-2-(N-((2E)-5-(tert-butoxycarbonylamino)-5-methylhex-2-enoyl)-N-methylamino)-3-(2-naphthyl)propionyl)-N-methylamino)-3-phenylpropionylamino)-1,1-dimethylethyl acetate"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 221.0, "units": "MILLIGRAM"}}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: First, magnesium was added to 1-bromo-3,4,5-trimethoxybenzene as a starting material, as shown in Reaction 6, and then 3-iodobenzoyl chloride was added thereto to obtain a Compound 21 derivative [(3-iodophenyl)(3,4,5-trimethoxyphenyl)methanone]. Thus obtained compound (88 mg, 0.250 mmol) was dissolved in tetrahydrofuran (2.5 ml), and 2-(tributylstannyl)thiazole (135 μl, 0.425 mmol) and Pd(PPh3)2Cl2 (8.79 mg, 0.012 mmol) were slowly added thereto at room temperature. The mixture was refluxed for 2 hours. After completion of the reaction, the reaction mixture was diluted with EtOAc, and an aqueous sodium bicarbonate solution was added thereto. An organic layer was extracted out from the resulting solution. The organic layer was washed with water, and brine, and dried over anhydrous MgSO4. The solid substance was filtered off, and the filtrate was vacuum concentrated. The resulting residue was purified by column chromatography (SiO2, n-Hex/EA=2/1→1/1) to obtain Compound 581 (20 mg, 22%) in a form of a yellow solid. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "3-iodobenzoyl chloride"}], "reaction_role": "REACTANT"}]}, "m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "magnesium"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1-bromo-3,4,5-trimethoxybenzene"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "as shown in Reaction 6"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "Compound 21"}], "reaction_role": "PRODUCT"}, {"identifiers": [{"type": "NAME", "value": "(3-iodophenyl)(3,4,5-trimethoxyphenyl)methanone"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: To a solution of sodium iodide (2.11 g) in acetonitrile (84.3 mL) was added at room temperature chlorotrimethylsilane (1.78 mL) and the mixture was stirred for 30 min. Then, 1-cyclobutyl-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one (0.91 g) was added, and the mixture was stirred at room temperature for 30 min, and further refluxed for 3 hr. The reaction mixture was allowed to cool to room temperature, water was added, and the mixture was stirred for 30 min, and extracted with ethyl acetate. The organic layer was washed with aqueous sodium thiosulfate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was triturated with diisopropyl ether, and collected by filtration to give the title compound (800 mg). ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "REACTANT"}]}, "m1_m5_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium iodide"}], "amount": {"mass": {"value": 2.11, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "chlorotrimethylsilane"}], "amount": {"volume": {"value": 1.78, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "acetonitrile"}], "amount": {"volume": {"value": 84.3, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "1-cyclobutyl-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one"}], "amount": {"mass": {"value": 0.91, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "the mixture was stirred for 30 min"}, "conditions_are_dynamic": true}, "workups": [{"type": "STIRRING", "details": "the mixture was stirred at room temperature for 30 min", "duration": {"value": 30.0, "units": "MINUTE"}, "temperature": {"control": {"type": "AMBIENT"}}}, {"type": "TEMPERATURE", "details": "further refluxed for 3 hr", "duration": {"value": 3.0, "units": "HOUR"}}, {"type": "STIRRING", "details": "the mixture was stirred for 30 min", "duration": {"value": 30.0, "units": "MINUTE"}}, {"type": "EXTRACTION", "details": "extracted with ethyl acetate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "The organic layer was washed with aqueous sodium thiosulfate solution and saturated brine", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium thiosulfate"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "brine"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over anhydrous magnesium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "magnesium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated under reduced pressure"}, {"type": "CUSTOM", "details": "The residue was triturated with diisopropyl ether", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "diisopropyl ether"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "collected by filtration"}], "outcomes": [{"reaction_time": {"value": 30.0, "units": "MINUTE"}, "products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 800.0, "units": "MILLIGRAM"}}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 91.9}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: A mixture of (R)-1-phenyl-ethanol (60.6 g, 0.496 mol), pyridine (42.5 mL, 0.526 mol) and 2-methyl-tetrahydrofuran (600 mL) was cooled to 0° C. and p-nitrophenyl chloroformate (100 g, 0.496 mol) was added over 15 min keeping the internal temperature below 5° C. The reaction mixture was warmed to room temperature and stirred for 2 h. To the reaction mixture was added 1.0 M HCl in water (300 mL). Layers were separated. The organic layer was washed with 1N HCl (300 mL) and brine (300 mL), filtered, concentrated to dryness by rotary evaporation, and dried under vacuum to give the title compound (140 g) as a clear yellow oil. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "p-nitrophenyl chloroformate"}], "amount": {"mass": {"value": 100.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "(R)-1-phenyl-ethanol"}], "amount": {"mass": {"value": 60.6, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "pyridine"}], "amount": {"volume": {"value": 42.5, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-methyl-tetrahydrofuran"}], "amount": {"volume": {"value": 600.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m5_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "HCl"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 300.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 0.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "stirred for 2 h"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "the internal temperature below 5\u00b0 C"}, {"type": "TEMPERATURE", "details": "The reaction mixture was warmed to room temperature", "temperature": {"control": {"type": "AMBIENT"}}}, {"type": "CUSTOM", "details": "Layers were separated"}, {"type": "WASH", "details": "The organic layer was washed with 1N HCl (300 mL) and brine (300 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "HCl"}], "amount": {"volume": {"value": 300.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "brine"}], "amount": {"volume": {"value": 300.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CONCENTRATION", "details": "concentrated to dryness by rotary evaporation"}, {"type": "CUSTOM", "details": "dried under vacuum"}], "outcomes": [{"reaction_time": {"value": 2.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 140.0, "units": "GRAM"}}}], "isolated_color": "clear yellow", "texture": {"type": "OIL", "details": "oil"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: p-Chlorobenzaldehyde (3.5 g., 0.025 mole) in ethanol (10 ml.) is added to a solution of 4-(o-chlorobenzyl)-4-phenyl-5-oxohexanoic acid (4.89 g., 0.015 mole) and sodium hydroxide (0.80 g., 0.03 mole) in water (50 ml.). The resulting mixture is heated on a steam bath for 24 hours. The reaction solution is cooled to room temperature, acidified with dilute hydrochloric acid (10 ml.), and the sticky solid which forms after scratching is filtered and air-dried, yield 7.0 g., m.p. 190°-213°C. Several recrystallizations from nitromethane, followed by a final recrystallization from acetonitrile, gives a light yellow solid with m.p. 223°-227°C. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m5_m2_m3_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "p-Chlorobenzaldehyde"}], "amount": {"mass": {"value": 3.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4-(o-chlorobenzyl)-4-phenyl-5-oxohexanoic acid"}], "amount": {"mass": {"value": 4.89, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium hydroxide"}], "amount": {"mass": {"value": 0.8, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "The resulting mixture is heated on a steam bath for 24 hours", "duration": {"value": 24.0, "units": "HOUR"}}, {"type": "FILTRATION", "details": "the sticky solid which forms after scratching is filtered"}, {"type": "CUSTOM", "details": "air-dried"}, {"type": "CUSTOM", "details": "Several recrystallizations from nitromethane", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "nitromethane"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "recrystallization from acetonitrile", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "acetonitrile"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "gives a light yellow solid with m.p. 223\u00b0-227\u00b0C."}], "outcomes": [{"products": [{}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: Activity assays were performed in 20 mL glass vials in a total volume of 500 μL 50 mM HEPES, pH7.2, 100 mM KCl, 7.5 mM MgCl2, 20 μM MgCl2, 5% (v/v) glycerol, 5 mM DTT with 50 μL protein and either 2 mM cis-FPP (2Z-6Z-farnesyl diphosphate), trans-FPP (E-E-farnesyl diphosphate), GPP (geranyl diphosphate), NDP (neryl diphosphate), or GGPP (geranylgeranyl diphosphate) as a substrate (Echelon Biosciences Incorporated, Salt Lake City, USA). Vials were closed with a teflon lined crimp cap immediately and incubated under moderate shaking for 1 hour at 30° C. ### ORD JSON:

{"inputs": {"m11": {"components": [{"identifiers": [{"type": "NAME", "value": "teflon"}], "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "HEPES"}], "reaction_role": "REACTANT"}]}, "m10": {"components": [{"identifiers": [{"type": "NAME", "value": "GGPP"}], "reaction_role": "REACTANT"}]}, "m12": {"components": [{"identifiers": [{"type": "NAME", "value": "glass"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "MgCl2"}], "reaction_role": "REACTANT"}]}, "m4": {"components": [{"identifiers": [{"type": "NAME", "value": "MgCl2"}], "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "2Z-6Z-farnesyl diphosphate"}], "reaction_role": "REACTANT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "DTT"}], "reaction_role": "REACTANT"}]}, "m9": {"components": [{"identifiers": [{"type": "NAME", "value": "NDP"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "KCl"}], "reaction_role": "REACTANT"}]}, "m8": {"components": [{"identifiers": [{"type": "NAME", "value": "GPP"}], "reaction_role": "REACTANT"}]}, "m7": {"components": [{"identifiers": [{"type": "NAME", "value": "E-E-farnesyl diphosphate"}], "reaction_role": "REACTANT"}]}, "m13": {"components": [{"identifiers": [{"type": "NAME", "value": "glycerol"}], "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 30.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "under moderate shaking for 1 hour at 30\u00b0 C."}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "crimp cap immediately"}], "outcomes": [{"reaction_time": {"value": 1.0, "units": "HOUR"}, "products": [{}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: (S,E)-N-((4-Chloro-3-fluoropyridin-2-yl)methylene)-2-methylpropane-2-sulfinamide: A solution of (R)-2-methylpropane-2-sulfinamide (0.540 g, 4.32 mmol), 4-chloro-3-fluoropicolinaldehyde (0.627 g, 3.93 mmol) and Cs2CO3 (1.921 g, 5.89 mmol) in DCM (20 mL) was stirred for 1 h at rt. The reaction mixture was diluted with EtOAc and washed with brine (3×20 mL). The organic layer was dried over MgSO4, filtered and concentrated in vacuo to provide the desired product (1.1 g, 100%). MS (ESI) m/z: 263.0 (M+H)+. ### ORD JSON:

{"inputs": {"m1_m2_m3_m4_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "(S,E)-N-((4-Chloro-3-fluoropyridin-2-yl)methylene)-2-methylpropane-2-sulfinamide"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "(R)-2-methylpropane-2-sulfinamide"}], "amount": {"mass": {"value": 0.54, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4-chloro-3-fluoropicolinaldehyde"}], "amount": {"mass": {"value": 0.627, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Cs2CO3"}], "amount": {"mass": {"value": 1.921, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DCM"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "EtOAc"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "WASH", "details": "washed with brine (3\u00d720 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "brine"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "The organic layer was dried over MgSO4", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "MgSO4"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CONCENTRATION", "details": "concentrated in vacuo"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "desired product"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 1.1, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 100.0}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: The above compound may be made analogous to Example 1 using ethyl 1-(6-((2,6-dimethylbenzyl)amino)-4-oxo-3,4-dihydroquinazolin-2-yl)-1H-pyrazole-4-carboxylate in step D and cyclopropylamine in step E. MS (ESI/CI): predicted mass C24H24N6O2, 428.2. ### ORD JSON:

{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl 1-(6-((2,6-dimethylbenzyl)amino)-4-oxo-3,4-dihydroquinazolin-2-yl)-1H-pyrazole-4-carboxylate"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "cyclopropylamine"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: 2,6-Difluoro-5-(trimethylsilyl)pyridine-3-carboxylic acid (1.17 g, 5.05 mmol) was dissolved in a mixture of DCM (20 mL) and MeOH (5 mL) and treated with (trimethylsilyl)diazomethane (2.0 m in diethyl ether, 5.0 mL, 10.00 mmol). [2,6-Difluoro-5-(trimethylsilyl)pyridine-3-carboxylic acid was synthesized according to M. Schlosser and T. Rausis, Eur. J. Org. Chem., 2004, pp 1018-1024]. The derived solution was maintained at rt for 1 hour. Evaporation under reduced pressure and purification using the by silica gel chromatography (hexane to ethyl actetate gradient) gave the desired methyl 2,6-difluoro-5-(trimethylsilyl)nicotinate. ### ORD JSON:

{"inputs": {"m2_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "2,6-Difluoro-5-(trimethylsilyl)pyridine-3-carboxylic acid"}], "amount": {"mass": {"value": 1.17, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DCM"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "MeOH"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "(trimethylsilyl)diazomethane"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "Evaporation"}, {"type": "CUSTOM", "details": "under reduced pressure and purification"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "2,6-Difluoro-5-(trimethylsilyl)pyridine-3-carboxylic acid"}], "reaction_role": "PRODUCT"}, {"identifiers": [{"type": "NAME", "value": "methyl 2,6-difluoro-5-(trimethylsilyl)nicotinate"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: A 1-liter electromagnetically stirred cylindrical glass reactor was charged with 5.0 g of crude ;b 1-nitroanthraquinone having a purity of 81% and containing 8% of 1,5-dinitroanthraquinone, 4% of 1,8-dinitroanthraquinone and 7% of other dinitroanthraquinones as impurities (0.016 mole of 1-mitroanthraquinone), 100 g of a 4% aqueous solution of sodium hydroxide and 4.2 g (0.067 mole) of 80% hydrated hydrazine. The mixture was stirred at 80° to 100° C. for 3 hours to form a slurry of 1-aminoanthraquinone. The slurry was cooled to room temperature, and 0.1 g of 5% palladium-carbon was added. The inside of the reactor was purged with hydrogen, and the crude 1-mitroanthraquinone was hydrogenated at room temperature. The reaction was stopped when 0.016 mole of hydrogen was absorbed. The catalyst and insoluble materials were separated by filtration. The filtrate was oxidized with air at 20° to 30° C. for 2 hours with stirring to afford 3.2 g of 1-aminoanthraquinone having a purity of 98% and containing 1% of 1,8-diaminoanthraquinone and only traces of other diaminoanthraquinones as impurities. The yield of 1-aminoanthraquinone was 88% on a purity basis. ### ORD JSON:

{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "1-nitroanthraquinone"}], "amount": {"mass": {"value": 5.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2_m3_m4_m5_m6_m7": {"components": [{"identifiers": [{"type": "NAME", "value": "1,5-dinitroanthraquinone"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1,8-dinitroanthraquinone"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dinitroanthraquinones"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "aqueous solution"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium hydroxide"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "hydrated hydrazine"}], "amount": {"mass": {"value": 4.2, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "The mixture was stirred at 80\u00b0 to 100\u00b0 C. for 3 hours"}, "conditions_are_dynamic": true}, "outcomes": [{"reaction_time": {"value": 3.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "1-aminoanthraquinone"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: To the compound of Example 54 (0.5 g) in THF (10 ml) and ethanol (20 ml) at room temperature was added sodium hydroxide (2N). The reaction mixture was stirred overnight at room temperature. The solution was evaporated under vacuo and then redissolved in H20. To the resulting solution was added acetic acid (1 ml). The yellow solid was filtered to give the title compound. ### ORD JSON:

{"inputs": {"m1_m3_m4_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "compound"}], "amount": {"mass": {"value": 0.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium hydroxide"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "THF"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "The reaction mixture was stirred overnight at room temperature"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The solution was evaporated under vacuo"}, {"type": "DISSOLUTION", "details": "redissolved in H20"}, {"type": "ADDITION", "details": "To the resulting solution was added acetic acid (1 ml)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "acetic acid"}], "amount": {"volume": {"value": 1.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "The yellow solid was filtered"}], "outcomes": [{"reaction_time": {"value": 8.0, "precision": 8.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: A mixture of 5-hydroxy-3-(quinol-4-ylmethylene)-2-oxindole (2.883 g, 10 mmol) and phosphoric acid 85% (13 g) and phosphorous pentoxide (10 g) was heated for 2 h at 60° C. The usual work-up gave the title compound in about 50% yield. ### ORD JSON:

{"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "5-hydroxy-3-(quinol-4-ylmethylene)-2-oxindole"}], "amount": {"mass": {"value": 2.883, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "phosphoric acid"}], "amount": {"mass": {"value": 13.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "phosphorous pentoxide"}], "amount": {"mass": {"value": 10.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 60.0, "units": "CELSIUS"}}, "conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 50.0}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: A concentrated solution of 50 g of KOH in approximately 30 ml of water is slowly added dropwise to a solution of 26.5 g of malonic acid dinitrile in approximately 250 ml of dimethyl formamide to which 45 ml of carbon disulphide have been added. During the addition the mixture is stirred and kept at a temperature of 0°-10° C. by cooling. After 10 minutes, 60.0 g of methyl iodide are slowly added dropwise while stirring and cooling and then, after 30 minutes, 30.5 g of chloroacetonitrile. The cooling bath is removed and 4.0 g of powdered KOH are added, the temperature of the reaction mixture rising to approximately 42° C. After stirring for another hour at 30°-35°° C., 600 ml of water and 100 ml of diethyl ether are added, after which the formed precipitate is sucked off, washed successively with water, isopropyl alcohol and diethyl ether, and dried. The desired product is obtained in a yield of 54.5 g and sublimates at 260° C. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "chloroacetonitrile"}], "amount": {"mass": {"value": 30.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m1_m6_m2_m7_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "KOH"}], "amount": {"mass": {"value": 50.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "malonic acid dinitrile"}], "amount": {"mass": {"value": 26.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "carbon disulphide"}], "amount": {"volume": {"value": 45.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 30.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "dimethyl formamide"}], "amount": {"volume": {"value": 250.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl iodide"}], "amount": {"mass": {"value": 60.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "is stirred"}, "conditions_are_dynamic": true}, "workups": [{"type": "ADDITION", "details": "have been added"}, {"type": "ADDITION", "details": "During the addition the mixture"}, {"type": "CUSTOM", "details": "kept at a temperature of 0\u00b0-10\u00b0 C."}, {"type": "TEMPERATURE", "details": "by cooling"}, {"type": "STIRRING", "details": "while stirring"}, {"type": "TEMPERATURE", "details": "cooling"}, {"type": "WAIT", "details": "after 30 minutes", "duration": {"value": 30.0, "units": "MINUTE"}}, {"type": "CUSTOM", "details": "The cooling bath is removed"}, {"type": "ADDITION", "details": "4.0 g of powdered KOH are added", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "KOH"}], "amount": {"mass": {"value": 4.0, "units": "GRAM"}}, "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "rising to approximately 42\u00b0 C", "temperature": {"setpoint": {"value": 42.0, "units": "CELSIUS"}}}, {"type": "STIRRING", "details": "After stirring for another hour at 30\u00b0-35\u00b0\u00b0 C"}, {"type": "ADDITION", "details": ", 600 ml of water and 100 ml of diethyl ether are added", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 600.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "diethyl ether"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "washed successively with water, isopropyl alcohol and diethyl ether", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "isopropyl alcohol"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "diethyl ether"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "dried"}], "outcomes": [{"reaction_time": {"value": 10.0, "units": "MINUTE"}, "products": [{"identifiers": [{"type": "NAME", "value": "desired product"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: To a solution of 3-chloro-2-methylbenzoic acid (1.00 g, 5.86 mmol) in methanol (25 mL) was added 3 drops of sulfuric acid. The mixture was stirred at reflux for 18 h. After concentrating the residue was dissolved in ether, washed with 10% sodium hydroxide solution, brine and dried (Na2SO4). Removal of the solvent under reduced pressure gave 0.95 g (88%) of the title compound as a white solid: 1H NMR (250 MHz, CDCl3) d 7.62 (d, 1 H), 7.41 (d, 1 H), 7.05 (t, 1 H), 3.82 (s, 3 H), 2.55 (s, 3 H). ### ORD JSON:

{"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "3-chloro-2-methylbenzoic acid"}], "amount": {"mass": {"value": 1.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methanol"}], "amount": {"volume": {"value": 25.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sulfuric acid"}], "reaction_role": "CATALYST"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "The mixture was stirred"}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "at reflux for 18 h", "duration": {"value": 18.0, "units": "HOUR"}}, {"type": "CONCENTRATION", "details": "After concentrating the residue"}, {"type": "DISSOLUTION", "details": "was dissolved in ether", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ether"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "washed with 10% sodium hydroxide solution, brine", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium hydroxide"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "brine"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried (Na2SO4)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Na2SO4"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "Removal of the solvent under reduced pressure"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.95, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 88.0}}], "isolated_color": "white", "texture": {"type": "CUSTOM", "details": "solid"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: A solution, cooled to 0° C., of 770 mg (3.51 mmol) of 8-methoxychromancarboxylic acid and 586 mg (3.83 mmol) of 1-hydroxybenzotriazole in 20 ml of anhydrous dichloromethane is treated with 723 mg (3.51 mmol) of dicyclohexylcarbodiimide and stirred for 5 min. A solution of 700 mg (3.19 mmol) of the compound from Example II and 0.88 ml (8.00 mmol) of N-methylmorpholine in 20 ml of dichloromethane is then added dropwise, and the reaction mixture may be stirred at room temperature for 1 h. The resultant urea is then removed by filtration, the filtrate is concentrated in vacuo and the crude product is purified by chromatography on 150 g of silica gel (dichloromethane/methanol 95:5). The product-containing fractions are collected, the solvent is evaporated in vacuo, and the residue is triturated with diethyl ether, filtered off with suction and dried in a high vacuum. 1.24 g (95%) of the title compound are obtained as colourless crystals. ### ORD JSON:

{"inputs": {"m1_m2_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "8-methoxychromancarboxylic acid"}], "amount": {"mass": {"value": 770.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1-hydroxybenzotriazole"}], "amount": {"mass": {"value": 586.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m4_m5_m7": {"components": [{"identifiers": [{"type": "NAME", "value": "compound"}], "amount": {"mass": {"value": 700.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "N-methylmorpholine"}], "amount": {"volume": {"value": 0.88, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "dicyclohexylcarbodiimide"}], "amount": {"mass": {"value": 723.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "stirred for 5 min"}, "conditions_are_dynamic": true}, "workups": [{"type": "STIRRING", "details": "the reaction mixture may be stirred at room temperature for 1 h", "duration": {"value": 1.0, "units": "HOUR"}, "temperature": {"control": {"type": "AMBIENT"}}}, {"type": "CUSTOM", "details": "The resultant urea is then removed by filtration", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "urea"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "the filtrate is concentrated in vacuo"}, {"type": "CUSTOM", "details": "the crude product is purified by chromatography on 150 g of silica gel (dichloromethane/methanol 95:5)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "crude product"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "dichloromethane methanol"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "The product-containing fractions are collected"}, {"type": "CUSTOM", "details": "the solvent is evaporated in vacuo"}, {"type": "CUSTOM", "details": "the residue is triturated with diethyl ether", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "diethyl ether"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered off with suction"}, {"type": "CUSTOM", "details": "dried in a high vacuum"}], "outcomes": [{"reaction_time": {"value": 5.0, "units": "MINUTE"}, "products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 1.24, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 95.0}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 86.3}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: Prepared analogously as described for example D1 using methyl 2-methylproponate and 3-benzyloxy-4-methoxybenzoyl chloride as starting compounds. ### ORD JSON:

{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl 2-methylproponate"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "3-benzyloxy-4-methoxybenzoyl chloride"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "Prepared analogously"}], "outcomes": [{"products": [{}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: (14.3 mg, 43%); from 3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-5-trifluoromethoxy-1H-indole (Example 4h, 20 mg, 0.068 mmol) and 2,6-dichlorobenzoyl chloride (22.4 mg, 0.107 mmol), HRMS-FAB+ for C22H17N2O2ClF3, calculated MH+ : 469.06973; found: 469.07199. ### ORD JSON:

{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-5-trifluoromethoxy-1H-indole"}], "amount": {"mass": {"value": 20.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2,6-dichlorobenzoyl chloride"}], "amount": {"mass": {"value": 22.4, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: A mixture of 22.5 g (91.6 mmol) of 5-chloro-1-ethyl-3-(trifluoromethyl)pyrazole-4-carboxylic acid and 45 mL of thionyl chloride was prepared and heated to reflux with stirring for 3 hours. The slurry became a dark orange solution. The excess thionyl chloride and other volatiles were removed by evaporation under reduced pressure to obtain a dark brown oil. This was taken up in 250 mL of dichloromethane and the resulting solution was cooled to about 0° C. and treated with 100 mL of concentrated ammonium hydroxide, which was added dropwise with stirring and cooling. When the addition was complete, the mixture was allowed to warm to ambient temperature and stir over a 2-hour period. The solids were collected by filtration and washed with water (3×50 mL). The solids that formed in the filtrate due to evaporation of the dichloromethane were collected in the same way. The combined solids were washed with water (2×100 mL) and were then suspended in water for 2 hours, recollected by filtration, and dried in an oven under reduced pressure. The white solid obtained was 18.4 g of the title compound melting at 15°-152° C. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 250.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "5-chloro-1-ethyl-3-(trifluoromethyl)pyrazole-4-carboxylic acid"}], "amount": {"mass": {"value": 22.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "thionyl chloride"}], "amount": {"volume": {"value": 45.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "ammonium hydroxide"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 0.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "with stirring for 3 hours"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "was prepared"}, {"type": "TEMPERATURE", "details": "heated"}, {"type": "TEMPERATURE", "details": "to reflux"}, {"type": "CUSTOM", "details": "The excess thionyl chloride and other volatiles were removed by evaporation under reduced pressure", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "thionyl chloride"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "to obtain a dark brown oil"}, {"type": "ADDITION", "details": "was added dropwise"}, {"type": "STIRRING", "details": "with stirring"}, {"type": "TEMPERATURE", "details": "cooling"}, {"type": "ADDITION", "details": "When the addition"}, {"type": "TEMPERATURE", "details": "to warm to ambient temperature", "temperature": {"control": {"type": "AMBIENT"}}}, {"type": "STIRRING", "details": "stir over a 2-hour period"}, {"type": "FILTRATION", "details": "The solids were collected by filtration"}, {"type": "WASH", "details": "washed with water (3\u00d750 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "The solids that formed in the filtrate due to evaporation of the dichloromethane", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "were collected in the same way"}, {"type": "WASH", "details": "The combined solids were washed with water (2\u00d7100 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "WAIT", "details": "were then suspended in water for 2 hours", "duration": {"value": 2.0, "units": "HOUR"}, "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "recollected by filtration"}, {"type": "CUSTOM", "details": "dried in an oven under reduced pressure"}, {"type": "CUSTOM", "details": "The white solid obtained"}], "outcomes": [{"reaction_time": {"value": 3.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 18.4, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: Benzenesulfinic acid sodium salt (10.25 g) was added to a solution containing 5 ml of cyclohexenone and 30 ml of water, followed by the dropwise addition of 60 ml of 1N hydrochloric acid. The reaction mixture was stirred at room temperature for 24 hours. The crystals so precipitated were filtered and then washed with water, isopropanol and cold ethyl ether. After recrystallization from isopropanol, 5.74 g of 3-(phenylsulfonyl)-cyclohexan-1-one were obtained in the form of white crystals. Yield: 97% ### ORD JSON:

{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "Benzenesulfinic acid sodium salt"}], "amount": {"mass": {"value": 10.25, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "cyclohexenone"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 30.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "amount": {"volume": {"value": 60.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "The reaction mixture was stirred at room temperature for 24 hours"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The crystals so precipitated"}, {"type": "FILTRATION", "details": "were filtered"}, {"type": "WASH", "details": "washed with water, isopropanol and cold ethyl ether", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "isopropanol"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "ethyl ether"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "After recrystallization from isopropanol", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "isopropanol"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 24.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "3-(phenylsulfonyl)-cyclohexan-1-one"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 5.74, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 97.0}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: 24.5 g (0.05 M) of 4-bromo-penta-2trans-en-1yl triphenylphosphonim bromide [which can be prepared according to the above given procedure] were slowly added to a suspension kept under stirring and in argon atmosphere of 13.5 g (0.12 M) of potassium ter-butoxide in 100 ml of anhydrous ether. The reaction mixture was kept under stirring overnight, whereupon 5 g (0.05 M) of hexanal in 35 ml of anhydrous ether were added thereto at a temperature of ca. 15°-25°. After having been left at 35° for 1 h, the mixture was cooled to room temperature, diluted with 130 ml of hexane, filtered over Celite and the clear filtrate, after washing with a saturated aqueous solution of NH4Cl and drying over magnesium sulphate, was kept 1 day at -20°. A subsequent purification was carried out by column chromatography by using 100 g of silica gel and elution with hexane. By distillation of the residue obtained on evaporation of the volatile portion of the eluate, 2.8 g (37%) of a mixture comprising 44:56 parts by weight of hydrocarbons Ic and Id was obtained. ### ORD JSON:

{"inputs": {"m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "potassium ter-butoxide"}], "amount": {"mass": {"value": 13.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ether"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "hexanal"}], "amount": {"mass": {"value": 5.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ether"}], "amount": {"volume": {"value": 35.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "hexane"}], "amount": {"volume": {"value": 130.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "24.5 g (0.05 M) of 4-bromo-penta-2trans-en-1yl triphenylphosphonim bromide [which can be prepared"}, {"type": "ADDITION", "details": "were slowly added to a suspension"}, {"type": "ADDITION", "details": "were added"}, {"type": "CUSTOM", "details": "at a temperature of ca. 15\u00b0-25\u00b0"}, {"type": "FILTRATION", "details": "filtered over Celite"}, {"type": "WASH", "details": "the clear filtrate, after washing with a saturated aqueous solution of NH4Cl", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "NH4Cl"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "drying over magnesium sulphate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "magnesium sulphate"}], "reaction_role": "WORKUP"}]}}, {"type": "WAIT", "details": "was kept 1 day at -20\u00b0", "duration": {"value": 1.0, "units": "DAY"}}, {"type": "CUSTOM", "details": "A subsequent purification"}, {"type": "WASH", "details": "100 g of silica gel and elution with hexane", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "hexane"}], "reaction_role": "WORKUP"}]}}, {"type": "DISTILLATION", "details": "By distillation of the residue"}], "outcomes": [{"reaction_time": {"value": 1.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "mixture"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 2.8, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 37.0}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 30.1}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: Ammonia gas was bubbled through a solution of 3-chloro-6-(4-fluorophenyl)-1,2,4-triazine (600 mg, 0.0029 mol) in tetrahydrofuran (8 mL) for 5 min at −40° C. The reaction mixture was sealed and heated at 50° C. for 2 hours. The mixture was concentrated under reduced pressure to yield the desired product (550 mg) which was directly used in the next step without further purification. LCMS: (M+H)=209.1. ### ORD JSON:

{"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "Ammonia"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "3-chloro-6-(4-fluorophenyl)-1,2,4-triazine"}], "amount": {"mass": {"value": 600.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tetrahydrofuran"}], "amount": {"volume": {"value": 8.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 50.0, "units": "CELSIUS"}}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The reaction mixture was sealed"}, {"type": "CONCENTRATION", "details": "The mixture was concentrated under reduced pressure"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "desired product"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 550.0, "units": "MILLIGRAM"}}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: To a solution of 1-{1-[9-methyl-8-(1H-pyrazol-4-yl)-9H-purin-6-yl]piperidin-4-yl}-1,3-dihydro-2H-benzimidazol-2-one (30 mg, 0.07 mmol) in DMF (0.5 mL) were added (bromomethyl)cyclobutane (0.02 mL, 0.18 mmol), and sodium bicarbonate (9 mg, 0.11 mmol). The reaction mixture was heated to 100° C. for 24 hours. The product was purified by preparatory HPLC (reverse-phase, acetonitrile/water with 0.1% formic acid) to give 7 mg (23% yield) of the title compound. 1H NMR (400 MHz, DMSO-d6): δ 10.85 (s, 1H), 8.42 (s, 1H), 8.25 (s, 1H), 8.01 (t, 1H), 7.13 (dd, 1H), 6.95-6.90 (m, 3H), 4.62-4.45 (m, 1H), 4.21 (d, 2H), 3.86-3.82 (m, 3H), 2.79 (dt, 1H), 2.40-2.25 (m, 2H), 2.01-1.92 (m, 2H), 1.87-1.70 (m, 6H); MS (EI) for C26H29N9O: 484.5 (MH+). ### ORD JSON:

{"inputs": {"m1_m4_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "1-{1-[9-methyl-8-(1H-pyrazol-4-yl)-9H-purin-6-yl]piperidin-4-yl}-1,3-dihydro-2H-benzimidazol-2-one"}], "amount": {"mass": {"value": 30.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "(bromomethyl)cyclobutane"}], "amount": {"volume": {"value": 0.02, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium bicarbonate"}], "amount": {"mass": {"value": 9.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DMF"}], "amount": {"volume": {"value": 0.5, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 100.0, "units": "CELSIUS"}}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The product was purified by preparatory HPLC (reverse-phase, acetonitrile/water with 0.1% formic acid)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "acetonitrile water"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "formic acid"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 7.0, "units": "MILLIGRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 23.0}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: To a mixed solution containing 1,280 g of potassium 4-chloro-3-nitrobenzenesulfonate, 1,150 ml of acetonitrile, 250 ml of Sulfolane (tetrahydrothiophene 1,1-dioxide) and 30 ml of dimethylacetamide was dropwise added 1,250 ml of phoshporus oxychloride under an inside temperature at 60° C. to 70° C. After the reaction was continued for 3 hours at 73° C., the reaction mixture was cooled with water, and thereto was slowly added 400 ml of water. The thus obtained product was poured into 5 liters of ice-cold water. The crystalline precipitate was filtered off, washed with water, and dried. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "oxychloride"}], "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 400.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m7": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "SOLVENT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "ice"}], "amount": {"volume": {"value": 5.0, "units": "LITER"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m3_m8": {"components": [{"identifiers": [{"type": "NAME", "value": "potassium 4-chloro-3-nitrobenzenesulfonate"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "acetonitrile"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Sulfolane"}], "amount": {"volume": {"value": 250.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dimethylacetamide"}], "amount": {"volume": {"value": 30.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "at 60\u00b0 C. to 70\u00b0 C"}, {"type": "FILTRATION", "details": "The crystalline precipitate was filtered off"}, {"type": "WASH", "details": "washed with water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "dried"}], "outcomes": [{"reaction_time": {"value": 3.0, "units": "HOUR"}, "products": [{}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: To a solution of 1-cyclopropyl-6-fluoro-7-bromo-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.58 g) in N-methyl-2-pyrrolidone (5 ml) is added 4-oxopiperidine (0.64 g) and the mixture is heated at 90° C. for 20 minutes The solvent is distilled off under reduced pressure To the resulting residue is added ethanol and the precipitated crystals are filtered to give 1-cyclopropyl-6-fluoro-7-(4-oxo-1-piperidinyl)-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (230 mg). ### ORD JSON:

{"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "1-cyclopropyl-6-fluoro-7-bromo-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid"}], "amount": {"mass": {"value": 0.58, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4-oxopiperidine"}], "amount": {"mass": {"value": 0.64, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "N-methyl-2-pyrrolidone"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 90.0, "units": "CELSIUS"}}, "conditions_are_dynamic": true}, "workups": [{"type": "DISTILLATION", "details": "is distilled off under reduced pressure To the resulting residue"}, {"type": "ADDITION", "details": "is added ethanol", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethanol"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "the precipitated crystals are filtered"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "1-cyclopropyl-6-fluoro-7-(4-oxo-1-piperidinyl)-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 230.0, "units": "MILLIGRAM"}}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: To a solution of (S)-2-amino-N-(2-(benzyloxy)-5-(pyridin-4-yl)phenyl)-3-phenylpropanamide 13.F (200 mg, 0.473 mmol) in methanol (2 mL) was added 10% Pd on carbon by weight (50 mg). The air was evacuated from the reaction flask and was replaced with hydrogen. The resulting slurry was stirred overnight at room temperature. The reaction mixture was filtered and the mother liquor condensed. The crude material was purified by reverse phase preparative HPLC to afford (S)-2-amino-N-(2-hydroxy-5-(pyridin-4-yl)phenyl)-3-phenylpropanamide 13.G (100 mg, 63% yield). ### ORD JSON:

{"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "(S)-2-amino-N-(2-(benzyloxy)-5-(pyridin-4-yl)phenyl)-3-phenylpropanamide"}], "amount": {"mass": {"value": 200.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methanol"}], "amount": {"volume": {"value": 2.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "Pd on carbon"}], "reaction_role": "CATALYST"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "The resulting slurry was stirred overnight at room temperature"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The air was evacuated from the reaction flask"}, {"type": "FILTRATION", "details": "The reaction mixture was filtered"}, {"type": "CUSTOM", "details": "the mother liquor condensed"}, {"type": "CUSTOM", "details": "The crude material was purified by reverse phase preparative HPLC", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "crude material"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 8.0, "precision": 8.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "(S)-2-amino-N-(2-hydroxy-5-(pyridin-4-yl)phenyl)-3-phenylpropanamide"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 100.0, "units": "MILLIGRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 63.0}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 63.4}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: 1-(2-Methoxy-5-trifluoromethyl-phenyl)-3-(2-trifluoromethyl-phenyl)-urea (1 g) was dissolved in dry dichloromethane (20 ml) and cooled in an ice-bath. A 1M solution of BBr3 in dichloromethane (4 ml) was added drop-wise, and the solution stirred at room temperature for 30 minutes. Water was added, and after vigorous stirring, the mixture was extracted with dichloromethane. Drying (MgSO4), filtration, concentration in vacuo and flash chromatography provided a product which was slurried with petrol, filtered, washed with petrol and dried to afford 1-(2-Hydroxy-5-trifluoromethyl-phenyl)-3-(2-trifluoromethyl-phenyl)-urea (340 mg). Mp.=158-159° C. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Water"}], "reaction_role": "REACTANT"}]}, "m7": {"components": [{"identifiers": [{"type": "NAME", "value": "petrol"}], "reaction_role": "SOLVENT"}]}, "m2_m3_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "solution"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "BBr3"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 4.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "1-(2-Methoxy-5-trifluoromethyl-phenyl)-3-(2-trifluoromethyl-phenyl)-urea"}], "amount": {"mass": {"value": 1.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "the solution stirred at room temperature for 30 minutes"}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "cooled in an ice-bath"}, {"type": "EXTRACTION", "details": "after vigorous stirring, the mixture was extracted with dichloromethane", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "Drying"}, {"type": "FILTRATION", "details": "(MgSO4), filtration, concentration in vacuo and flash chromatography", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "MgSO4"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "provided a product which"}, {"type": "FILTRATION", "details": "filtered"}, {"type": "WASH", "details": "washed with petrol", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "petrol"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "dried"}], "outcomes": [{"reaction_time": {"value": 30.0, "units": "MINUTE"}, "products": [{"identifiers": [{"type": "NAME", "value": "1-(2-Hydroxy-5-trifluoromethyl-phenyl)-3-(2-trifluoromethyl-phenyl)-urea"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 340.0, "units": "MILLIGRAM"}}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: 1-Cyclopentyl-7-methoxy-3-methyl-1H-pyrimido[5,4-c]quinoline-2,4-dione (18 mg) was prepared from 4-cyclopentylamino-8-methoxy-quinoline-3-carboxylic acid ethyl ester (0.1 mmol) and methyl isocyanate (0.5 mmol) following general procedure C. LCMS: m/z 326 [M+1]+. ### ORD JSON:

{"inputs": {"m0_m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-cyclopentylamino-8-methoxy-quinoline-3-carboxylic acid ethyl ester"}], "amount": {"moles": {"value": 0.1, "units": "MILLIMOLE"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methyl isocyanate"}], "amount": {"moles": {"value": 0.5, "units": "MILLIMOLE"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "1-Cyclopentyl-7-methoxy-3-methyl-1H-pyrimido[5,4-c]quinoline-2,4-dione"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 18.0, "units": "MILLIGRAM"}}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: A solution of 2-chloro-6-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoro-4-iodonicotinonitrile (Method 39, 0.28 g, 0.69 mmol), (5)-1-(4-fluorophenyl)ethanamine (0.19 g, 1.3 mmol), and DIEA (0.11 g, 0.90 mmol) in n-BuOH (1 ml) was heated to 140° C. for 18 hours. The reaction was diluted with water (10 ml), extracted with DCM (2×20 ml) and the combined organic fractions were dried over Na2SO4, filtered, and then concentrated. The resulting oil was purified by column chromatography (DCM-MeOH=100:1) to give the title compound (0.07 g, 20%). MS: Calcd.: 506. Found: [M+H]+ 507. ### ORD JSON:

{"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "2-chloro-6-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-fluoro-4-iodonicotinonitrile"}], "amount": {"mass": {"value": 0.28, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "(5)-1-(4-fluorophenyl)ethanamine"}], "amount": {"mass": {"value": 0.19, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DIEA"}], "amount": {"mass": {"value": 0.11, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "n-BuOH"}], "amount": {"volume": {"value": 1.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "EXTRACTION", "details": "extracted with DCM (2\u00d720 ml)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "DCM"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "the combined organic fractions were dried over Na2SO4", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Na2SO4"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CONCENTRATION", "details": "concentrated"}, {"type": "CUSTOM", "details": "The resulting oil was purified by column chromatography (DCM-MeOH=100:1)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "DCM MeOH"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.07, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 20.0}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 20.0}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: To a solution of benzyl (4-{[tert-butyl(dimethyl)silyl]oxy}-2-cyclopropylphenyl)acetate (586 mg) in tetrahydrofuran (6.89 mL) was added a 1 M solution of tetra-n-butylammonium fluoride in tetrahydrofuran (2.23 mL) under ice-cooling, followed by stirring at room temperature overnight. To a reaction solution was added water, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution in this order, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain benzyl (2-cyclopropyl-4-hydroxyphenyl)acetate (398 mg). ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "REACTANT"}]}, "m1_m5_m2_m3_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "benzyl (4-{[tert-butyl(dimethyl)silyl]oxy}-2-cyclopropylphenyl)acetate"}], "amount": {"mass": {"value": 586.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "solution"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tetra-n-butylammonium fluoride"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tetrahydrofuran"}], "amount": {"volume": {"value": 6.89, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "tetrahydrofuran"}], "amount": {"volume": {"value": 2.23, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "by stirring at room temperature overnight"}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "cooling"}, {"type": "EXTRACTION", "details": "followed by extraction with ethyl acetate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "The organic layer was washed with water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "a saturated aqueous sodium chloride solution in this order, then dried over anhydrous sodium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium chloride"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "sodium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated under reduced pressure"}, {"type": "CUSTOM", "details": "The residue was purified by silica gel column chromatography (hexane-ethyl acetate)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "hexane ethyl acetate"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 8.0, "precision": 8.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "benzyl (2-cyclopropyl-4-hydroxyphenyl)acetate"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 398.0, "units": "MILLIGRAM"}}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: A mixed solution of ethanol (100 mL) and methanol (100 mL) of (E)-1-acetyl-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]pyrrolidin-2-one (7.5 g) and potassium carbonate (1.6 g) was agitated at room temperature for 2 hours. After condensing reaction solution to ⅓, added to iced water and ethyl acetate and deposited solids were separated by filtration to obtain 4.7 g of the title compound. Furthermore, the filtrate was extracted with ethyl acetate and the organic layer was dried over anhydrous magnesium sulfate after washed with a saturated saline solution. This solution was concentrated and the deposited solids was obtained by filtration to yield 2.7 g of the title compound. The physical properties of the compound are as follows. ### ORD JSON:

{"inputs": {"m6_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "SOLVENT"}]}, "m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methanol"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "(E)-1-acetyl-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]pyrrolidin-2-one"}], "amount": {"mass": {"value": 7.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "potassium carbonate"}], "amount": {"mass": {"value": 1.6, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "After condensing reaction solution to \u2153"}, {"type": "CUSTOM", "details": "were separated by filtration"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 4.7, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: Following the general procedure outlined in Example 3, 1-azabicyclo[2.2.2]oct -4-yl{bis[3-(methyloxy)phenyl]}methanol (0.0538 g, 0.152 mmol) and 2-bromoethyl phenylmethyl ether (0.0361 mL, 0.228 mmol) in 2 CH3CN/3CHCl3 (4.0 mL) were reacted to give the desired product (0.0292 g, 33.8%). EI-MS m/z 488(M+) Rt (2.03 min). ### ORD JSON:

{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "1-azabicyclo[2.2.2]oct -4-yl{bis[3-(methyloxy)phenyl]}methanol"}], "amount": {"mass": {"value": 0.0538, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2-bromoethyl phenylmethyl ether"}], "amount": {"volume": {"value": 0.0361, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "CH3CN"}], "reaction_role": "SOLVENT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "were reacted"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "desired product"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.0292, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 33.8}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 33.8}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: 3-Furoic acid (2.4 g) and HATU (8.15 g) in DMF (25 ml) were stirred at room temperature for 15 min. HOBT (2.9 g), 3-iodomethylaniline (5.0 g) and DIPEA (11.2 ml) were added and the mixture was stirred at room temp for 16 h. The solvent was evaporated under vacuum and the residue was partitioned between ethyl acetate (100 ml) and aqueous sodium carbonate (10%, 100 ml). The aqueous layer was extracted with ethyl acetate (50 ml) and the combined organic phases were washed with hydrochloric acid (2N, 75 ml), water (75 ml) and brine (75 ml). The organic phase was dried (magnesium sulphate) and absorbed onto silica. The silica was applied to a silica column and eluted with cyclohexane/ethyl acetate (3:1) to give the title compound. ### ORD JSON:

{"inputs": {"m1_m2_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "3-Furoic acid"}], "amount": {"mass": {"value": 2.4, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "HATU"}], "amount": {"mass": {"value": 8.15, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DMF"}], "amount": {"volume": {"value": 25.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "HOBT"}], "amount": {"mass": {"value": 2.9, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "3-iodomethylaniline"}], "amount": {"mass": {"value": 5.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DIPEA"}], "amount": {"volume": {"value": 11.2, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "the mixture was stirred at room temp for 16 h"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The solvent was evaporated under vacuum"}, {"type": "CUSTOM", "details": "the residue was partitioned between ethyl acetate (100 ml) and aqueous sodium carbonate (10%, 100 ml)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "sodium carbonate"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "EXTRACTION", "details": "The aqueous layer was extracted with ethyl acetate (50 ml)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "the combined organic phases were washed with hydrochloric acid (2N, 75 ml), water (75 ml) and brine (75 ml)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "amount": {"volume": {"value": 75.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 75.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "brine"}], "amount": {"volume": {"value": 75.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "The organic phase was dried (magnesium sulphate)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "magnesium sulphate"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "absorbed onto silica"}, {"type": "WASH", "details": "eluted with cyclohexane/ethyl acetate (3:1)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "cyclohexane ethyl acetate"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 16.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: This compound was made as a derivative of the compound prepared as described in Section 5.1.2.32. To a THF solution of 3-(4-hydroxyphenyl)naphtho[1,2-c]isoxazol-7-ol was added acetyl chloride (3.0 eq.) and pyridine (3.0 eq). The mixture was stirred at rt for 24 h, poured into cold NaHCO3, extracted with EtOAc. The organic extracts were washed with brine, dried with Na2SO4 and concentrated in vacuo to give the product as a white powder. ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "NaHCO3"}], "reaction_role": "REACTANT"}]}, "m5_m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "3-(4-hydroxyphenyl)naphtho[1,2-c]isoxazol-7-ol"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "acetyl chloride"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "pyridine"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "THF"}], "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "The mixture was stirred at rt for 24 h"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "prepared"}, {"type": "EXTRACTION", "details": "extracted with EtOAc", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "EtOAc"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "The organic extracts were washed with brine", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "brine"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried with Na2SO4", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Na2SO4"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated in vacuo"}], "outcomes": [{"reaction_time": {"value": 24.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "product"}], "isolated_color": "white", "texture": {"type": "POWDER", "details": "powder"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: After dissolving 1.012 g of triethylamine in 10 ml of ethanol, 2.575 g of 2-(2-fluorophenyl)-1-(piperidin-4-yl)ethanone hydrochloride, 10 ml of ethanol, 2.951 ml of titanium (IV) tetraisopropoxide and 760 mg of 2-acetyl-3-methoxypyrazine were added in that order and the mixture was stirred for 5 hours and 20 minutes at room temperature. Next, 1.59 g of sodium triacetoxyborohydride was added to the reaction mixture and the mixture was stirred overnight at room temperature. A sodium carbonate solution and ethyl acetate were added to the reaction mixture and the mixture was filtered with celite. The filtrate was extracted with ethyl acetate, and the extract was washed with water and saturated brine and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and then the residue was dissolved in ethyl acetate and filtered with silica gel. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (169 mg, 9% yield). ### ORD JSON:

{"inputs": {"m4_m8": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium carbonate"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "SOLVENT"}]}, "m9_m5_m1_m7_m6_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2-(2-fluorophenyl)-1-(piperidin-4-yl)ethanone hydrochloride"}], "amount": {"mass": {"value": 2.575, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-acetyl-3-methoxypyrazine"}], "amount": {"mass": {"value": 760.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "titanium (IV) tetraisopropoxide"}], "amount": {"volume": {"value": 2.951, "units": "MILLILITER"}}, "reaction_role": "CATALYST"}, {"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "triethylamine"}], "amount": {"mass": {"value": 1.012, "units": "GRAM"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium triacetoxyborohydride"}], "amount": {"mass": {"value": 1.59, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "the mixture was stirred for 5 hours and 20 minutes at room temperature"}, "conditions_are_dynamic": true}, "workups": [{"type": "ADDITION", "details": "were added in that order"}, {"type": "STIRRING", "details": "the mixture was stirred overnight at room temperature", "duration": {"value": 8.0, "precision": 8.0, "units": "HOUR"}, "temperature": {"control": {"type": "AMBIENT"}}}, {"type": "FILTRATION", "details": "the mixture was filtered with celite"}, {"type": "EXTRACTION", "details": "The filtrate was extracted with ethyl acetate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "the extract was washed with water and saturated brine", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "brine"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over anhydrous magnesium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "magnesium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "DISTILLATION", "details": "The solvent was distilled off under reduced pressure"}, {"type": "DISSOLUTION", "details": "the residue was dissolved in ethyl acetate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered with silica gel"}, {"type": "DISTILLATION", "details": "The solvent was distilled off under reduced pressure"}, {"type": "CUSTOM", "details": "the residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "n-hexane ethyl acetate"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 20.0, "units": "MINUTE"}, "products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 169.0, "units": "MILLIGRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 9.0}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 9.5}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: 50 mg of {4(S)-Azido-7(S)-butylcarbamoyl-5(S)-hydroxy-2(S)-isopropyl-8-methyl-1 (R,S)-[4- methoxy-3-(2-methoxymethoxyethyl)-phenyl]-nonyl}-isobutyrate are hydrogenated in 10 ml of methanol in the presence of 50 mg of 10% Pd/C at room temperature and normal pressure. The reaction mixture is filtered and concentrated by evaporation. The residue is purified by FC (2 g of silica gel, dichloromethane/methanol 9:1). The title compound is obtained: Rf (dichloromethane/methanol 9:1)=0.19; HPLC Rt =13.42 minutes; FAB-MS (M+H)+ =509. ### ORD JSON:

{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "{4(S)-Azido-7(S)-butylcarbamoyl-5(S)-hydroxy-2(S)-isopropyl-8-methyl-1 (R,S)-[4- methoxy-3-(2-methoxymethoxyethyl)-phenyl]-nonyl}-isobutyrate"}], "amount": {"mass": {"value": 50.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "methanol"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "Pd/C"}], "amount": {"mass": {"value": 50.0, "units": "MILLIGRAM"}}, "reaction_role": "CATALYST"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "FILTRATION", "details": "The reaction mixture is filtered"}, {"type": "CONCENTRATION", "details": "concentrated by evaporation"}, {"type": "CUSTOM", "details": "The residue is purified by FC (2 g of silica gel, dichloromethane/methanol 9:1)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "dichloromethane methanol"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: To a solution of 2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (200 mg, 1.0 mmol) in NMP (1 mL) were added powdered KOH (392 mg, 7.0 mmol) and 3-vinyl-benzo[b]thiophene (320 mg, 2.0 mmol). The reaction mixture was stirred at 90° C. for 5 h. The reaction mixture was diluted with water (15 mL) and extracted with EtOAc (3×20 mL). The combined organic layer was washed with water (5×25 mL), dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (3% MeOH-DCM) followed by reverse phase HPLC to yield 5-(2-benzo[b]thiophen-3-yl-ethyl)-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole. 1H NMR (CDCl3, freebase) δ (ppm): 7.82 (d, 1H), 7.6 (d, 1H), 7.38 (m, 2H), 7.2 (m, 2H), 7.0 (d, 1H), 6.93 (s, 1H), 4.3 (t, 2H), 3.62 (s, 2H), 3.5 (s, 3H), 3.21 (t, 2H), 2.63 (t, 2H), 2.41 (m, 5H). ### ORD JSON:

{"inputs": {"m1_m4_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole"}], "amount": {"mass": {"value": 200.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "KOH"}], "amount": {"mass": {"value": 392.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "3-vinyl-benzo[b]thiophene"}], "amount": {"mass": {"value": 320.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "NMP"}], "amount": {"volume": {"value": 1.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 15.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 90.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "The reaction mixture was stirred at 90\u00b0 C. for 5 h"}, "conditions_are_dynamic": true}, "workups": [{"type": "EXTRACTION", "details": "extracted with EtOAc (3\u00d720 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "EtOAc"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "The combined organic layer was washed with water (5\u00d725 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 25.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over anhydrous sodium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated"}, {"type": "CUSTOM", "details": "The residue was purified by silica gel column chromatography (3% MeOH-DCM)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "MeOH DCM"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 5.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "5-(2-benzo[b]thiophen-3-yl-ethyl)-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: A mixture of 9-methylphenanthrene (14.2 g, 74 mmol), benzoyl peroxide (40 mg, 0.16 mmol) and NBS (13.3 g, 74.6 mmol) in 210 mL of benzene was refluxed for 5 h. The reaction mixture was cooled to 0° C. and the succinimide precipitated was removed by filtration. The filtrate was washed by 15% NaOH, dried over MgSO4 and concentrated to yield 18 g of product which was used for the next step without further purification. ### ORD JSON:

{"inputs": {"m1_m4_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "9-methylphenanthrene"}], "amount": {"mass": {"value": 14.2, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "NBS"}], "amount": {"mass": {"value": 13.3, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "benzene"}], "amount": {"volume": {"value": 210.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "benzoyl peroxide"}], "amount": {"mass": {"value": 40.0, "units": "MILLIGRAM"}}, "reaction_role": "CATALYST"}]}}, "conditions": {"temperature": {"setpoint": {"value": 0.0, "units": "CELSIUS"}}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "was refluxed for 5 h", "duration": {"value": 5.0, "units": "HOUR"}}, {"type": "CUSTOM", "details": "the succinimide precipitated", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "succinimide"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "was removed by filtration"}, {"type": "WASH", "details": "The filtrate was washed by 15% NaOH", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "NaOH"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over MgSO4", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "MgSO4"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "product"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 18.0, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: A mixture of 4-(4-fluorophenyl)-3,3-dimethyl-1,2,3,6-tetrahydropyridine (450 mg, 2.192 mmol), palladium hydroxide on carbon (308 mg, 2.192 mmol), and acetic acid (1.5 mL, 26.2 mmol) in methanol (10 mL) was degassed under nitrogen/vacuum, then hydrogenated at 50 psi for two days. The catalyst was removed by filtration and rinsed with methanol, and the filtrate was concentrated in vacuo to yield the title compound (442 mg, 2.132 mmol, 97% yield) as a pale yellow oil. MS (ESI+)=208.29, (M+H)+. ### ORD JSON:

{"inputs": {"m1_m4_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(4-fluorophenyl)-3,3-dimethyl-1,2,3,6-tetrahydropyridine"}], "amount": {"mass": {"value": 450.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "acetic acid"}], "amount": {"volume": {"value": 1.5, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methanol"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "palladium hydroxide on carbon"}], "amount": {"mass": {"value": 308.0, "units": "MILLIGRAM"}}, "reaction_role": "CATALYST"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "was degassed under nitrogen/vacuum"}, {"type": "CUSTOM", "details": "The catalyst was removed by filtration"}, {"type": "WASH", "details": "rinsed with methanol", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "methanol"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "the filtrate was concentrated in vacuo"}], "outcomes": [{"reaction_time": {"value": 2.0, "units": "DAY"}, "products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "AMOUNT", "amount": {"moles": {"value": 2.132, "units": "MILLIMOLE"}}}, {"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 442.0, "units": "MILLIGRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 97.0}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 97.3}}], "isolated_color": "pale yellow", "texture": {"type": "OIL", "details": "oil"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: N-Benzyl-3-(4-formylphenyl)indole (9) and NaBH4 are allowed to react in the same manner as described above in the preparation of compound 7 to afford compound 10 in 51% yield. mp 122° C.; IR (cm−1): 3462, 1742; 1H NMR (CDCl3): δ 7.94–7.97 (m, 1H), 7.64–7.68 (d, 3H), 7.41–7.45 (d, 10H), 5.34 (s, 2H), 4.72 (s, 2H). HRMS: m/z 313.1466 (calculated for C22H19NO, 313.1467). ### ORD JSON:

{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "N-Benzyl-3-(4-formylphenyl)indole"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "NaBH4"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "compound 7"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "to react in the same manner"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "compound 10"}], "measurements": [{"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 51.0}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: The title compound was prepared as described in Example 51A, substituting 2-methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridin-1(2H)-yl)pyrimidine for 1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 4-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide for 4-bromoaniline. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.07-8.95 (m, 1H), 8.78 (dd, J=7.0, 0.5 Hz, 1H), 8.28-8.16 (m, 2H), 8.00 (d, J=2.0 Hz, 1H), 7.97-7.87 (m, 2H), 7.80-7.74 (m, 1H), 7.63-7.54 (m, 2H), 7.40 (dd, J=7.0, 1.5 Hz, 1H), 7.04 (d, J=7.4 Hz, 1H), 6.41-6.31 (m, 1H), 4.66 (m, 2H), 4.47 (m, 2H), 4.10 (t, J=5.8 Hz, 2H), 2.77-2.64 (m, 2H), 2.55 (s, 3H); MS (ESI(+)) m/e 425 (M+H)+. ### ORD JSON:

{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)benzamide"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "4-bromoaniline"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: The Friedel-Crafts reaction is performed by premixing about 1 molar equivalent of the appropriate thiazolone of formula 3 with about 1 molar equivalent to about 10 molar equivalents, preferably about 2 to 3 molar equivalents, of a Lewis acid catalyst in a suitable solvent, for example, petroleum ethers; a chlorinated aromatic, such as 1,2,4-trichlorobenzene or o-dichlorobenzene; carbon disulfide; nitrobenzene; or a chlorinated hydrocarbon such as carbon tetrachloride, ethylene chloride, methylene chloride, chloroform or preferably tetrachloroethane. About 1 molar equivalent to about 10 molar equivalents, preferably about 1.1 molar equivalents of the appropriate acid halide of formula 4 is added, preferably dropwise, to the mixture of thiazolone, Lewis acid, and solvent and the reaction is allowed to proceed for about 1/2 hour to about 100 hours, preferably from about 1 hour to about 10 hours depending on the reactants, the solvent, and the temperature which can be from about -78° to about 150° C., preferably about 60° to about 150° C., most preferably about 100°-120° C. Preferably the solvent is removed by distillation. The resulting heterocyclo- or acetyl- thiazolone may be isolated from the reaction mixture by any suitable art-known procedure, preferably by quenching the reaction mixture with ice water and subsequently removing the product by filtration or extraction and solvent removal or by quenching the cooled reaction mixture with hydrochloric acid and subsequently collecting the solid product by filtration. Purification can be accomplished by, for example, recrystallization, preferably from ethanol. ### ORD JSON:

{"inputs": {"m5": {"components": [{"identifiers": [{"type": "NAME", "value": "chlorinated hydrocarbon"}], "reaction_role": "REACTANT"}]}, "m16": {"components": [{"identifiers": [{"type": "NAME", "value": "o-dichlorobenzene"}], "reaction_role": "SOLVENT"}]}, "m4": {"components": [{"identifiers": [{"type": "NAME", "value": "nitrobenzene"}], "reaction_role": "REACTANT"}]}, "m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "thiazolone"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "formula 3"}], "reaction_role": "REACTANT"}]}, "m15": {"components": [{"identifiers": [{"type": "NAME", "value": "carbon disulfide"}], "reaction_role": "SOLVENT"}]}, "m9": {"components": [{"identifiers": [{"type": "NAME", "value": "thiazolone"}], "reaction_role": "REACTANT"}]}, "m7_m8": {"components": [{"identifiers": [{"type": "NAME", "value": "acid halide"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "formula 4"}], "reaction_role": "REACTANT"}]}, "m13": {"components": [{"identifiers": [{"type": "NAME", "value": "ethylene chloride"}], "reaction_role": "SOLVENT"}]}, "m11": {"components": [{"identifiers": [{"type": "NAME", "value": "chloroform"}], "reaction_role": "SOLVENT"}]}, "m10": {"components": [{"identifiers": [{"type": "NAME", "value": "petroleum ethers"}], "reaction_role": "SOLVENT"}]}, "m12": {"components": [{"identifiers": [{"type": "NAME", "value": "methylene chloride"}], "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "1,2,4-trichlorobenzene"}], "reaction_role": "REACTANT"}]}, "m14": {"components": [{"identifiers": [{"type": "NAME", "value": "carbon tetrachloride"}], "reaction_role": "SOLVENT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "tetrachloroethane"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The Friedel-Crafts reaction"}, {"type": "WAIT", "details": "to proceed for about 1/2 hour to about 100 hours, preferably from about 1 hour to about 10 hours"}, {"type": "CUSTOM", "details": "can be from about -78\u00b0 to about 150\u00b0 C., preferably about 60\u00b0 to about 150\u00b0 C., most preferably about 100\u00b0-120\u00b0 C"}, {"type": "CUSTOM", "details": "Preferably the solvent is removed by distillation"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "acetyl- thiazolone"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: The starting materials for this synthesis was 4-aminopyridine which was protected by boc group and converted to 4-tert-butoxycarbonylamino-nicotinic acid, depicted as formula 35 in Scheme 15, by ortholithiation followed by quenching with dry ice. This intermediate was reacted with trichloromethyl chloroformate to yield 1H-pyrido[4,3-d][1,3]oxazine-2,4-dione, depicted by formula 36 in Scheme 15, which was then converted to 4-chloro-2-oxo-1,2-dihydro-[1,6]-naphthyridine-3-carboxylic acid ethyl ester, depicted by formula 37 in Scheme 15. The reaction of 4-chloro-2-oxo-1,2-dihydro-[1,6]-naphthyridine-3-carboxylic acid ethyl ester with piperazine-1-yl-thiophene-2-yl-methanone gave 2-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1,2-dihydro-[1,6]-naphthyridin-3-carboxylic acid ethyl ester, depicted by formula 38 in Scheme 15, which was reacted with corresponding alkyl halides (R—X) to yield 1-N-substituted-2-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1,2-dihydro-[1,6]-naphthyridine-3-carboxylic acid ethyl esters as shown in Scheme 15. ### ORD JSON:

{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "formula 36"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-chloro-2-oxo-1,2-dihydro-[1,6]-naphthyridine-3-carboxylic acid ethyl ester"}], "reaction_role": "REACTANT"}]}, "m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "4-chloro-2-oxo-1,2-dihydro-[1,6]-naphthyridine-3-carboxylic acid ethyl ester"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "piperazine-1-yl-thiophene-2-yl-methanone"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "formula 37"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "2-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1,2-dihydro-[1,6]-naphthyridin-3-carboxylic acid ethyl ester"}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: 10.7 g of 8-amino-5-hydroxy-3,4-dihydrocarbostyril was dissolved in 100 ml of pyridine, and 10.0 g of cyclohexylcarbonyl chloride was added to the solution while vigorously stirring at room temperature followed by stirring at 50° C. for 30 minutes. The precipitated crystals were recovered by filtration, washed with ethanol, dried and dissolved in 200 ml of a 10% aqueous sodium hydroxide solution. Activated carbon was added to the solution, and the mixture was stirred and filtered. The filtrate was rendered acidic with hydrochloric acid under ice cooling, and the precipitated crystals were recovered by filtration, washed with water and dried. Recrystallization from methanol yielded 6.6 g of 8-cyclohexylcarbonylamino-5-hydroxy-3,4-dihydrocarbostyril as colorless amorphous crystals having a melting point of 304.2°-304.8° C. ### ORD JSON:

{"inputs": {"m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "8-amino-5-hydroxy-3,4-dihydrocarbostyril"}], "amount": {"mass": {"value": 10.7, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "pyridine"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "cyclohexylcarbonyl chloride"}], "amount": {"mass": {"value": 10.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "while vigorously stirring at room temperature"}, "conditions_are_dynamic": true}, "workups": [{"type": "STIRRING", "details": "by stirring at 50\u00b0 C. for 30 minutes", "duration": {"value": 30.0, "units": "MINUTE"}, "temperature": {"setpoint": {"value": 50.0, "units": "CELSIUS"}}}, {"type": "FILTRATION", "details": "The precipitated crystals were recovered by filtration"}, {"type": "WASH", "details": "washed with ethanol", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethanol"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "dried"}, {"type": "DISSOLUTION", "details": "dissolved in 200 ml of a 10% aqueous sodium hydroxide solution", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium hydroxide"}], "reaction_role": "WORKUP"}]}}, {"type": "ADDITION", "details": "Activated carbon was added to the solution"}, {"type": "STIRRING", "details": "the mixture was stirred"}, {"type": "FILTRATION", "details": "filtered"}, {"type": "FILTRATION", "details": "the precipitated crystals were recovered by filtration"}, {"type": "WASH", "details": "washed with water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "dried"}, {"type": "CUSTOM", "details": "Recrystallization from methanol", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "methanol"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "8-cyclohexylcarbonylamino-5-hydroxy-3,4-dihydrocarbostyril"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 6.6, "units": "GRAM"}}}], "isolated_color": "colorless amorphous", "texture": {"type": "CRYSTAL", "details": "crystals"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: 1 mmole of phosphorus pentachloride in benzene is added to a solution in benzene of 1 mmole of dibenzylphenylethyl phosphonate, which has been previously obtained. The mixture is refluxed at 70° C. for 3 to 4h under an anhydrous atmosphere until the chloride is completely obtained. The benzene of said mixture is then evaporated and is taken up in dichloromethane. This solution is used immediately for carrying out coupling with the peptide. ### ORD JSON:

{"inputs": {"m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "4h"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "chloride"}], "reaction_role": "REACTANT"}]}, "m1_m5_m6_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "phosphorus pentachloride"}], "amount": {"moles": {"value": 1.0, "units": "MILLIMOLE"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dibenzylphenylethyl phosphonate"}], "amount": {"moles": {"value": 1.0, "units": "MILLIMOLE"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "benzene"}], "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "benzene"}], "reaction_role": "SOLVENT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "has been previously obtained"}, {"type": "CUSTOM", "details": "is completely obtained"}, {"type": "CUSTOM", "details": "The benzene of said mixture is then evaporated", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "benzene"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: To a solution of ethyl 2,4-dioxo-4-phenylbutanoate (16.0 g) in ethanol (150 mL) was added hydrazine monohydrate (4.0 mL), and the mixture was heated under reflux for 3 hr. The reaction mixture was concentrated under reduced pressure, and the residue was crystallized from diisopropyl ether to give the title compound as a pale-brown solid (yield 12.0 g, 67%). ### ORD JSON:

{"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl 2,4-dioxo-4-phenylbutanoate"}], "amount": {"mass": {"value": 16.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "hydrazine monohydrate"}], "amount": {"volume": {"value": 4.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"volume": {"value": 150.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "the mixture was heated"}, {"type": "TEMPERATURE", "details": "under reflux for 3 hr", "duration": {"value": 3.0, "units": "HOUR"}}, {"type": "CONCENTRATION", "details": "The reaction mixture was concentrated under reduced pressure"}, {"type": "CUSTOM", "details": "the residue was crystallized from diisopropyl ether", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "diisopropyl ether"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 12.0, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 67.0}}], "isolated_color": "pale-brown", "texture": {"type": "CUSTOM", "details": "solid"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: To a mixture of 0.54 gm (1.8 mMol) 5-(4,5-dihydrothia-zol-5-yl)-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole in 20 mL trifluoroacetic acid were added slowly 320 μL (2 mMol) triethylsilane. The reaction mixture was stirred at room temperature for 18 hours and then concentrated under reduced pressure. The residual oil was partitioned between ethyl acetate and aqueous potassium carbonate. The organic phase was dried over sodium sulfate and concentrated under reduced pressure. The residue was crystallized from acetonitrile to provide 0.40 gm (74%) of the title compound compound as a crystalline solid. ### ORD JSON:

{"inputs": {"m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "5-(4,5-dihydrothia-zol-5-yl)-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole"}], "amount": {"mass": {"value": 0.54, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "trifluoroacetic acid"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "triethylsilane"}], "amount": {"volume": {"value": 320.0, "units": "MICROLITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "The reaction mixture was stirred at room temperature for 18 hours"}, "conditions_are_dynamic": true}, "workups": [{"type": "CONCENTRATION", "details": "concentrated under reduced pressure"}, {"type": "CUSTOM", "details": "The residual oil was partitioned between ethyl acetate and aqueous potassium carbonate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "potassium carbonate"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "The organic phase was dried over sodium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated under reduced pressure"}, {"type": "CUSTOM", "details": "The residue was crystallized from acetonitrile", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "acetonitrile"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 18.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.4, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 74.0}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 74.2}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: A 500 mL flask was charged with the 6-chloro-2-methylsulfanyl-pyrimidine-4-carboxylic acid methyl ester (4.37 g, 20 mmol), and chloroform (30 mL). Ammonia (57 mL, 7 M in methanol, 0.4 mol, 20 eq.) was added with stirring. HPLC analysis after 20 minutes indicated no starting methyl ester remained. The mixture was sparged with nitrogen for 30 min, then concentrated in vacuo, and dried under high vacuum to afford the 6-chloro-2-methylsulfanyl-pyrimidine-4-carboxylic acid amide (4.21 g, quant.) in sufficient purity for use in the next step. 1H NMR (500 MHz, CDCl3) □ 7.76 (s, 1H), 7.60 (br s, 1H), 5.97 (br s, 1H), 2.61 (s, 3H); ESI-MS m/z 204.1 (M+H)+. ### ORD JSON:

{"inputs": {"m1_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "6-chloro-2-methylsulfanyl-pyrimidine-4-carboxylic acid methyl ester"}], "amount": {"mass": {"value": 4.37, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "chloroform"}], "amount": {"volume": {"value": 30.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Ammonia"}], "amount": {"volume": {"value": 57.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl ester"}], "reaction_role": "REACTANT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "with stirring"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The mixture was sparged with nitrogen for 30 min", "duration": {"value": 30.0, "units": "MINUTE"}}, {"type": "CONCENTRATION", "details": "concentrated in vacuo"}, {"type": "CUSTOM", "details": "dried under high vacuum"}], "outcomes": [{"reaction_time": {"value": 20.0, "units": "MINUTE"}, "products": [{"identifiers": [{"type": "NAME", "value": "6-chloro-2-methylsulfanyl-pyrimidine-4-carboxylic acid amide"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 4.21, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: To 5-bromo-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide (20 mg, 0.048 mmol) was added 4-methyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2-piperazinone (31 mg, 0.097 mmol) in dioxane (3.0 mL) and H2O (1.0 mL), potassium carbonate (13 mg, 0.097 mmol) and chloro(di-2-norbornylphosphino)(2-dimethylaminomethylferrocen-1-yl)palladium (II) (10 mg, 0.016 mmol). The reaction mixture was reacted in a microwave at 160° C. for 10 min. The reaction mixture was heated in a microwave at 160° C. for 10 min. The reaction mixture was concentrated under Nitrogen and purified by Gilson Preparatory HPLC. The desired fraction in CH3CN and H2O was treated with saturated potassium carbonate to neutralize salts and then concentrated to give 1.9 mg the title compound (8%). ### ORD JSON:

{"inputs": {"m1_m2_m4_m5_m3_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "5-bromo-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide"}], "amount": {"mass": {"value": 20.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4-methyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2-piperazinone"}], "amount": {"mass": {"value": 31.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "potassium carbonate"}], "amount": {"mass": {"value": 13.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dioxane"}], "amount": {"volume": {"value": 3.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "H2O"}], "amount": {"volume": {"value": 1.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "chloro(di-2-norbornylphosphino)(2-dimethylaminomethylferrocen-1-yl)palladium (II)"}], "amount": {"mass": {"value": 10.0, "units": "MILLIGRAM"}}, "reaction_role": "CATALYST"}]}}, "conditions": {"temperature": {"setpoint": {"value": 160.0, "units": "CELSIUS"}}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The reaction mixture was reacted in a microwave at 160\u00b0 C. for 10 min", "duration": {"value": 10.0, "units": "MINUTE"}, "temperature": {"setpoint": {"value": 160.0, "units": "CELSIUS"}}}, {"type": "CONCENTRATION", "details": "The reaction mixture was concentrated under Nitrogen"}, {"type": "CUSTOM", "details": "purified by Gilson Preparatory HPLC"}, {"type": "ADDITION", "details": "The desired fraction in CH3CN and H2O was treated with saturated potassium carbonate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "CH3CN"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "H2O"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "potassium carbonate"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 1.9, "units": "MILLIGRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 8.0}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 7.6}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: 6-(Hydroxymethyl)-8,9-dihydro-1H-furo[3,4-f]isochromen-3(6H)-one, in DCM (10 mL) was treated with p-Toluenesulfonyl chloride (0.40 g, 2.3 mmol); to the mixture was added pyridine (2 mL) and the resulting mixture stirred at room temperature for 12 h. TLC (hexanes/EtOAc=10.5) and LC indicated the consumption of starting material and formation of the desired product. Dichloromethane was added to the reaction mixture and it was washed with NaCl, water and dried over Na2SO4, filtered and concentrated to dryness, absorbed onto silica gel and was then subjected to purification over silica gel; the title compound was isolated with the solvent system of hexanes/EtOAc (10.5). 1H-NMR (400 MHz, CDCl3) δ ppm 7.781 (d, J=8 Hz, 1H), 7.727 (d, J=8 Hz, 1H), 7.367 (d, J=8 Hz, 1H), 7.257 (d, J=8.5 Hz, 1H), 7.206 (d, J=8 Hz, 1H), 5.253 (s, 2H), 5.110 (s, 1H), 4.481-4.452 (m, 2H), 4.419-4.385 (m, 2H), 4.196-4.153 (m, 2H), 2.495 (s, 3H). ### ORD JSON:

{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "pyridine"}], "amount": {"volume": {"value": 2.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m2_m6_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "6-(Hydroxymethyl)-8,9-dihydro-1H-furo[3,4-f]isochromen-3(6H)-one"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "p-Toluenesulfonyl chloride"}], "amount": {"mass": {"value": 0.4, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DCM"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "hexanes EtOAc"}], "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "the resulting mixture stirred at room temperature for 12 h"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "the consumption of starting material and formation of the desired product", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "desired product"}], "reaction_role": "WORKUP"}]}}, {"type": "ADDITION", "details": "Dichloromethane was added to the reaction mixture and it", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Dichloromethane"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "was washed with NaCl, water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "NaCl"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over Na2SO4", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Na2SO4"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CONCENTRATION", "details": "concentrated to dryness"}, {"type": "CUSTOM", "details": "absorbed onto silica gel"}, {"type": "CUSTOM", "details": "was then subjected to purification over silica gel"}], "outcomes": [{"reaction_time": {"value": 12.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "reaction_role": "PRODUCT"}, {"reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: To a suspension of 95.3 g of 2-formyl-3,5-dimethoxy-6-methylbenzoic acid methyl ester in 250 ml of dichloromethane were added 800 ml of a 1M solution of boron trichloride in dichloromethane over 40 min at a temperature of 5°-10° C. The mixture was allowed to warm to 20° C. within 30 min and stirring was continued at room temperature for 4 h. The clear solution was cooled to 5° C. and then poured into a mixture of 1.5 l of ice-water and 0.5 l of dichloromethane. The layers were separated and the aqueous phase was back-extracted with 0.4 l of dichloromethane. The organic layers were washed with water, dried over sodium sulfate and evaporated in vacuo. Crystallization of the residual material from ethyl acetate/hexane provided 77.3 g of 2-formyl-3-hydroxy-5-methoxy-6-methylbenzoic acid methyl ester as colorless crystals of m.p. 118°-119° C. ### ORD JSON:

{"inputs": {"m4_m7": {"components": [{"identifiers": [{"type": "NAME", "value": "ice water"}], "amount": {"volume": {"value": 1.5, "units": "LITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 0.5, "units": "LITER"}}, "reaction_role": "SOLVENT"}]}, "m2_m3_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "solution"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "boron trichloride"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "reaction_role": "SOLVENT"}]}, "m1_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "2-formyl-3,5-dimethoxy-6-methylbenzoic acid methyl ester"}], "amount": {"mass": {"value": 95.3, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 250.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 20.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "stirring"}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "The clear solution was cooled to 5\u00b0 C.", "temperature": {"setpoint": {"value": 5.0, "units": "CELSIUS"}}}, {"type": "CUSTOM", "details": "The layers were separated"}, {"type": "EXTRACTION", "details": "the aqueous phase was back-extracted with 0.4 l of dichloromethane", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 0.4, "units": "LITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "The organic layers were washed with water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over sodium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "evaporated in vacuo"}, {"type": "CUSTOM", "details": "Crystallization of the residual material from ethyl acetate/hexane", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate hexane"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 4.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "2-formyl-3-hydroxy-5-methoxy-6-methylbenzoic acid methyl ester"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 77.3, "units": "GRAM"}}}], "isolated_color": "colorless", "texture": {"type": "CRYSTAL", "details": "crystals"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: A solution of 7-methoxy-8-[(2R)-oxiran-2-ylmethoxy]-2,3-dihydroimidazo[1,2-c]quinazolin-5-amine (Intermediate F, 0.195 g, 0.68 mmol) and 8-oxa-3-azabicyclo[3.2.1]octane hydrochloride (0.506 g, 3.38 mmol, 10 equiv.) in DMF (4.5 mL) was heated in a microwave reactor for 45 min. at 140° C. The resulting mixture was concentrated under reduced pressure. The residue was treated with a 4:1 CH2Cl2/isopropanol solution (25 mL), washed with a saturated sodium bicarbonate solution (25 mL), dried (anh. sodium sulfate) and concentrated under reduced pressure. The resulting residue was purified using MPLC to give N-(8-{[(2R)-2-hydroxy-3-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)propyl]oxy}-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-ylamine (0.74 g, 16%): HPLC ret. time 0.70 min.; mass spectrum m/z 402 ((M+1)+, 7%). ### ORD JSON:

{"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "7-methoxy-8-[(2R)-oxiran-2-ylmethoxy]-2,3-dihydroimidazo[1,2-c]quinazolin-5-amine"}], "amount": {"mass": {"value": 0.195, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Intermediate F"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "8-oxa-3-azabicyclo[3.2.1]octane hydrochloride"}], "amount": {"mass": {"value": 0.506, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DMF"}], "amount": {"volume": {"value": 4.5, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CONCENTRATION", "details": "The resulting mixture was concentrated under reduced pressure"}, {"type": "ADDITION", "details": "The residue was treated with a 4:1 CH2Cl2/isopropanol solution (25 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "CH2Cl2 isopropanol"}], "amount": {"volume": {"value": 25.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "washed with a saturated sodium bicarbonate solution (25 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium bicarbonate"}], "amount": {"volume": {"value": 25.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried (anh. sodium sulfate)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated under reduced pressure"}, {"type": "CUSTOM", "details": "The resulting residue was purified"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "8-{[(2R)-2-hydroxy-3-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)propyl]oxy}-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-ylamine"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.74, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 16.0}}], "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: Ethyl 2-(3-amino-5-bromo-4-hydroxyphenyl)-4-methylpentanoate 1 (4 g, 0.012 mol) was dissolved in a mixture of ACN/H2O/HCl 60 mL/30 mL/8 mL at 0° C. A solution of NaNO2 (0.919 g, 1.1 eq) in water (10 mL) was added dropwise at 0° C. and the reaction mixture was stirred for 1 h at 0° C. A solution of CuCl (5.99 g, 0.060 mol) in water (10 mL) was added dropwise to the reaction mixture at 0° C. The reaction mixture was then heated to 50° C. for 2.5 h. upon which the mixture was poured into ice water, extracted with ethyl acetate (3×100 mL) The combined organic layers were washed with water (200 mL) and brine (100 mL), dried over NaSO4 and concentrated in vacuo to give crude black oil which was purified by chromatography over silica gel (hexane/EtOAc) to give ethyl 2-(3-bromo-5-chloro-4-hydroxyphenyl)-4-methylpentanoate as yellow oil 2.2 g, (47.3%). 1H NMR (CDCl3, 200 MHz): 7.38 (s, 1H); 7.4 (s, 1H); 5.80 (bs, 1H); 4.13 (q, 2H); 3.51 (t, 1H); 1.93-1.56 (m, 2H); 1.51 (m, 1H); 1.21 (t, 3H), 0.97 (d, 6H); ### ORD JSON:

{"inputs": {"m3": {"components": [{"identifiers": [{"type": "NAME", "value": "ice water"}], "reaction_role": "REACTANT"}]}, "m1_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Ethyl 2-(3-amino-5-bromo-4-hydroxyphenyl)-4-methylpentanoate"}], "amount": {"mass": {"value": 4.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ACN H2O HCl"}], "amount": {"volume": {"value": 60.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "NaNO2"}], "amount": {"mass": {"value": 0.919, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m7_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "CuCl"}], "amount": {"mass": {"value": 5.99, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}}, "conditions": {"temperature": {"setpoint": {"value": 0.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "the reaction mixture was stirred for 1 h at 0\u00b0 C"}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "The reaction mixture was then heated to 50\u00b0 C. for 2.5 h. upon which the mixture", "duration": {"value": 2.5, "units": "HOUR"}, "temperature": {"setpoint": {"value": 50.0, "units": "CELSIUS"}}}, {"type": "EXTRACTION", "details": "extracted with ethyl acetate (3\u00d7100 mL) The combined organic layers", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "were washed with water (200 mL) and brine (100 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "brine"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over NaSO4", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "NaSO4"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated in vacuo"}, {"type": "CUSTOM", "details": "to give crude black oil which"}, {"type": "CUSTOM", "details": "was purified by chromatography over silica gel (hexane/EtOAc)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "hexane EtOAc"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 1.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "ethyl 2-(3-bromo-5-chloro-4-hydroxyphenyl)-4-methylpentanoate"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 2.2, "units": "GRAM"}}}], "isolated_color": "yellow", "texture": {"type": "OIL", "details": "oil"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: HCl (4N in dioxane, 5 mL) was added to 3-{3,5-dichloro-4-[4-(6-methylpyrimidin-4-ylamino)thiazolo[5,4-c]pyridin-2-yl]-phenyl}-azetidine-1-carboxylic acid tert-butyl ester (0.062 g, 0.114 mmol). The suspension was heated at 40° C. for 1 hour and then cooled to room temperature. The volatiles were removed under reduced pressure and the resultant residue was triturated with a mixture of EtOAc/DCM and then purified by column chromatography on silica gel eluting with 0-5% 2N NH3/MeOH in DCM to afford the title compound as an off-white solid (20 mg, 40% yield). 1H NMR (400 MHz, CDCl3): δ 8.65 (d, J=1.2 Hz, 1H), 8.46 (d, J=5.6 Hz, 1H), 7.84 (d, J=5.6 Hz, 1H), 7.75 (s, 2H), 7.63 (s, 1H), 3.99-3.90 (m, 1H), 3.85 (t, J=7.6 Hz, 2H), 3.61 (t, J=6.9 Hz, 2H), 2.41 (s, 3H). LCMS (Method C): RT=2.21 min, m/z: 443 [M+H+]. ### ORD JSON:

{"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "HCl"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "3-{3,5-dichloro-4-[4-(6-methylpyrimidin-4-ylamino)thiazolo[5,4-c]pyridin-2-yl]-phenyl}-azetidine-1-carboxylic acid tert-butyl ester"}], "amount": {"mass": {"value": 0.062, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 40.0, "units": "CELSIUS"}}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "cooled to room temperature", "temperature": {"control": {"type": "AMBIENT"}}}, {"type": "CUSTOM", "details": "The volatiles were removed under reduced pressure"}, {"type": "CUSTOM", "details": "the resultant residue was triturated with a mixture of EtOAc/DCM", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "resultant residue"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "EtOAc DCM"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "purified by column chromatography on silica gel eluting with 0-5% 2N NH3/MeOH in DCM", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "NH3 MeOH"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "DCM"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 20.0, "units": "MILLIGRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 40.0}}], "isolated_color": "off-white", "texture": {"type": "CUSTOM", "details": "solid"}, "reaction_role": "PRODUCT"}]}]}

Below is a description of an organic reaction. Extract information from it to an ORD JSON record. The specific format is as follows:{"inputs": {"{component_id}": {"components": [{"identifiers": [{"type": "NAME", "value": "{chemical_name}"}], "amount": {"{amount_type}": {"value": {amount_value}, "units": "{amount_units}"}}, "reaction_role": "{reaction_role}"}]}}, "conditions": {"temperature": {"setpoint": {"value": {temperature_value}, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "{stirring_details}"}}, "workups": [{"type": "{workup_type}", "details": "{workup_details}", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "{workup_component}"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": {reaction_time_value}, "precision": {reaction_time_precision}, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "{product_name}"}], "measurements": [{"type": "AMOUNT", "amount": {"mass": {"value": {product_mass}, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]} ### Procedure: A mixture of 4-bromo-2-(trifluoromethyl)pyridine (282 mg), tripotassium phosphate (481 mg), picolinic acid (27.9 mg), copper (I) iodide (21.58 mg) and 4-(2-amino-5-chloropyridin-3-yl)phenol (250 mg) in DMSO (5 ml) was stirred at 140° C. under N2 overnight. The mixture was poured into sat. NH4Cl aq. and extracted with EtOAc. The organic layer was separated, washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with EtOAc in hexane) to give the title compound (230 mg) as a pale yellow solid. ### ORD JSON:

{"inputs": {"m5": {"components": [{"identifiers": [{"type": "NAME", "value": "NH4Cl"}], "reaction_role": "REACTANT"}]}, "m1_m2_m3_m7_m4_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "4-bromo-2-(trifluoromethyl)pyridine"}], "amount": {"mass": {"value": 282.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tripotassium phosphate"}], "amount": {"mass": {"value": 481.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "picolinic acid"}], "amount": {"mass": {"value": 27.9, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4-(2-amino-5-chloropyridin-3-yl)phenol"}], "amount": {"mass": {"value": 250.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DMSO"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "copper (I) iodide"}], "amount": {"mass": {"value": 21.58, "units": "MILLIGRAM"}}, "reaction_role": "CATALYST"}]}}, "conditions": {"temperature": {"setpoint": {"value": 140.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "was stirred at 140\u00b0 C. under N2 overnight"}, "conditions_are_dynamic": true}, "workups": [{"type": "EXTRACTION", "details": "extracted with EtOAc", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "EtOAc"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "The organic layer was separated"}, {"type": "WASH", "details": "washed with brine", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "brine"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over anhydrous magnesium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "magnesium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated in vacuo"}, {"type": "CUSTOM", "details": "The residue was purified by column chromatography (NH silica gel, eluted with EtOAc in hexane)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "EtOAc"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "hexane"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 8.0, "precision": 8.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 230.0, "units": "MILLIGRAM"}}}], "isolated_color": "pale yellow", "texture": {"type": "CUSTOM", "details": "solid"}, "reaction_role": "PRODUCT"}]}]}