Datasets:

Ivywake
/

USPTO2_modified

Dataset card Viewer Files Files and versions Community

Split (1)

train · 80k rows

instruction stringlengths 151 5.17k	output stringlengths 291 4.64k	input stringclasses 1 value
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A solution of (2-fluoro-5-methylphenyl)methanamine (1-f, 50 mg, 0.26 mmol, Oakwood Products, Inc., West Columbia, S.C.) and diisopropylethylamine (88 uL, 0.52 mmol) in dichloromethane (1 mL) was treated at room temperature with 2-phenylbutanoyl chloride (1-a, 47 mg, 0.26 mmol). The reaction mixture was stirred for 30 min, partitioned between dichloromethane and 0.1N—NaOH. The aqueous layer was removed and the organic layer washed with 0.1N-HCl. The aqueous layer was removed by filtering through a plastic frit. The organic layer was evaporated in vacuo to give the desired product (1-2); HRMS (M+1)=286.1586. ### ORD JSON:	{"inputs": {"m1_m2_m4_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "(2-fluoro-5-methylphenyl)methanamine"}], "amount": {"mass": {"value": 50.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "diisopropylethylamine"}], "amount": {"volume": {"value": 88.0, "units": "MICROLITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-phenylbutanoyl chloride"}], "amount": {"mass": {"value": 47.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 1.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "The reaction mixture was stirred for 30 min"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "partitioned between dichloromethane and 0.1N\u2014NaOH", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "NaOH"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "The aqueous layer was removed"}, {"type": "WASH", "details": "the organic layer washed with 0.1N-HCl", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "HCl"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "The aqueous layer was removed"}, {"type": "FILTRATION", "details": "by filtering through a plastic frit"}, {"type": "CUSTOM", "details": "The organic layer was evaporated in vacuo"}], "outcomes": [{"reaction_time": {"value": 30.0, "units": "MINUTE"}, "products": [{"reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To a solution of 3-(4-fluorophenyl)-1,2,3,4-tetrahydroquinoline (0.25 g, 0.0011 mol) in ethanol (1.2 mL) was added 1N hydrochloric acid (1.2 mL). The reaction mixture was cooled to 0° C., and to this a cold solution of sodium nitrite (0.151 g, 0.0022 mol) in water (3.0 mL) was added at the same temperature. The reaction mixture was warmed to RT and stirred for 1 h. After completion of reaction (monitored by TLC), solvent was removed under reduced pressure to obtain product as a brown colored oil (0.27 g). ### ORD JSON:	{"inputs": {"m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium nitrite"}], "amount": {"mass": {"value": 0.151, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 3.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1_m4_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "3-(4-fluorophenyl)-1,2,3,4-tetrahydroquinoline"}], "amount": {"mass": {"value": 0.25, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "amount": {"volume": {"value": 1.2, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"volume": {"value": 1.2, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 0.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "stirred for 1 h"}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "The reaction mixture was warmed to RT", "temperature": {"control": {"type": "AMBIENT"}}}, {"type": "CUSTOM", "details": "After completion of reaction (monitored by TLC), solvent"}, {"type": "CUSTOM", "details": "was removed under reduced pressure"}], "outcomes": [{"reaction_time": {"value": 1.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "product"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.27, "units": "GRAM"}}}], "isolated_color": "brown colored", "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. ### Procedure: Potassium carbonate (1.00 g, 7.28 mmol) was added to a flask charged with 2-amino-8-ethyl-4-methyl-6-((trimethylsilyl)ethynyl)pyrido[2,3-d]pyrimidin-7(8H)-one (1.09 g, 3.64 mmol) in anhydrous methanol (15 mL). The reaction was stirred at room temperature under nitrogen for 16 h. The reaction was concentrated to one half volume and the yellow precipitate collected by vacuum filtration to afford 2-amino-8-ethyl-6-ethynyl-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one. ### ORD JSON:	{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "Potassium carbonate"}], "amount": {"mass": {"value": 1.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "2-amino-8-ethyl-4-methyl-6-((trimethylsilyl)ethynyl)pyrido[2,3-d]pyrimidin-7(8H)-one"}], "amount": {"mass": {"value": 1.09, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methanol"}], "amount": {"volume": {"value": 15.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "The reaction was stirred at room temperature under nitrogen for 16 h"}, "conditions_are_dynamic": true}, "workups": [{"type": "CONCENTRATION", "details": "The reaction was concentrated to one half volume"}, {"type": "FILTRATION", "details": "the yellow precipitate collected by vacuum filtration"}], "outcomes": [{"reaction_time": {"value": 16.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "2-amino-8-ethyl-6-ethynyl-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one"}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: In analogy to example 166, step 1, 5-{3-(4-bromo-2-fluoro-phenyl)-1-[(E)-hydroxyimino]-3-o-tolyl-propyl}-1-methyl-1H-pyridin-2-one (example 193, step 4) was reacted with 3-fluoro-4-methoxycarbonylphenylboronic acid in the presence of dichloro(1,1′-bis(diphenylphosphino)-ferrocene)palladium(II) dichloromethane adduct in a mixture of 1,4-dioxane, water and 2 M aqueous sodium carbonate solution to give the title compound as a light brown solid, MS (ESI+): m/z=517.4 [M+H]+. ### ORD JSON:	{"inputs": {"m1_m2_m6_m5_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "5-{3-(4-bromo-2-fluoro-phenyl)-1-[(E)-hydroxyimino]-3-o-tolyl-propyl}-1-methyl-1H-pyridin-2-one"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "3-fluoro-4-methoxycarbonylphenylboronic acid"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium carbonate"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1,4-dioxane"}], "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "dichloro(1,1\u2032-bis(diphenylphosphino)-ferrocene)palladium(II) dichloromethane adduct"}], "reaction_role": "CATALYST"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "isolated_color": "light 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. ### Procedure: To a solution of 4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-5-methyl-pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid ethyl ester (68 mg 0.19 mmol) in anhydrous methylene chloride (2.0 mL) at −78° C. under argon was added DIBAL (0.48 mmol, 0.48 mL, 1.0M, 2.5 eq.) dropwise. After 5 minutes, the mixture was warmed to −15° C. and allowed to stir for an additional 15 minutes. A drop of ethanol was added to quench the reaction followed by IN sodium hydroxide (0.2 mL) and 1.0 mL of ethyl acetate and 1.0 mL of THF. After 30 minutes, the mixture was filtered to remove the resulting solid. The filtrate was dried, concentrated in vacuo, and chromatographed using silica gel eluting with 40-75% ethyl acetate in hexanes (gradient). Concentration of the desired fractions afforded the title compound (39 mg, 63%) as a clear oil. LC/MS; (M+H)+=327.3 ### ORD JSON:	{"inputs": {"m1_m4_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-5-methyl-pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid ethyl ester"}], "amount": {"mass": {"value": 68.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DIBAL"}], "amount": {"volume": {"value": 0.48, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methylene chloride"}], "amount": {"volume": {"value": 2.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "ethanol"}], "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": -15.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "to stir for an additional 15 minutes"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "to quench the reaction"}, {"type": "WAIT", "details": "After 30 minutes", "duration": {"value": 30.0, "units": "MINUTE"}}, {"type": "FILTRATION", "details": "the mixture was filtered"}, {"type": "CUSTOM", "details": "to remove the resulting solid"}, {"type": "CUSTOM", "details": "The filtrate was dried"}, {"type": "CONCENTRATION", "details": "concentrated in vacuo"}, {"type": "CUSTOM", "details": "chromatographed"}], "outcomes": [{"reaction_time": {"value": 5.0, "units": "MINUTE"}, "products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 39.0, "units": "MILLIGRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 63.0}}], "isolated_color": "clear", "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. ### Procedure: Sodium hydroxide (2.71 g, 67.7 mmol) was added to a solution of ethyl 1-[({3-[(ethoxyacetyl)amino]quinolin-4-yl}amino)methyl]cyclohexanecarboxylate hydrochloride (10.15 g, 22.6 mmol) in 9:1 ethanol/water (30 mL), and the solution was heated at reflux for several hours. The ethanol was removed under reduced pressure, and the resulting solution was diluted with water and adjusted to pH 4 to 5 with the addition of 3 M hydrochloric acid. The mixture was then extracted several times with dichloromethane The aqueous fraction was adjusted to pH 7 and extracted several more times with dichloromethane. The combined extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 5.73 g of 1-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclohexanecarboxylic acid. ### ORD JSON:	{"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "Sodium hydroxide"}], "amount": {"mass": {"value": 2.71, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethyl 1-[({3-[(ethoxyacetyl)amino]quinolin-4-yl}amino)methyl]cyclohexanecarboxylate hydrochloride"}], "amount": {"mass": {"value": 10.15, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethanol water"}], "amount": {"volume": {"value": 30.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "the solution was heated"}, {"type": "TEMPERATURE", "details": "at reflux for several hours"}, {"type": "CUSTOM", "details": "The ethanol was removed under reduced pressure", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethanol"}], "reaction_role": "WORKUP"}]}}, {"type": "ADDITION", "details": "the resulting solution was diluted with water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "ADDITION", "details": "adjusted to pH 4 to 5 with the addition of 3 M hydrochloric acid", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "reaction_role": "WORKUP"}]}}, {"type": "EXTRACTION", "details": "The mixture was then extracted several times with dichloromethane The aqueous fraction", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "reaction_role": "WORKUP"}]}}, {"type": "EXTRACTION", "details": "extracted several more times with dichloromethane", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "The combined extracts were dried over magnesium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "magnesium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CONCENTRATION", "details": "concentrated under reduced pressure"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "1-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclohexanecarboxylic acid"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 5.73, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To (2R)-4-(1-(6-(diethoxymethyl)-3-fluoropyridin-2-yl)azetidin-3-yl)-1,2-dimethylpiperazine (157 mg, 0.428 mmol) described in Production Example 24-1-2 was added formic acid (5.00 mL) at room temperature. The resultant mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under a reduced pressure, to give a crude product (125 mg) of the title compound. The product was used in the subsequent reaction without further purification. ### ORD JSON:	{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "(2R)-4-(1-(6-(diethoxymethyl)-3-fluoropyridin-2-yl)azetidin-3-yl)-1,2-dimethylpiperazine"}], "amount": {"mass": {"value": 157.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "resultant mixture"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "formic acid"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CONCENTRATION", "details": "The reaction mixture was concentrated under a reduced pressure"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "crude product"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 125.0, "units": "MILLIGRAM"}}}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 4-Fluoro-2-methoxyaniline (2.4 g, 17.00 mmol) was added portionwise to concentrated H2SO4 (15 mL) which was cooled in a ice/water bath, and where the temperature was kept below 15° C. during the addition. The mixture was stirred until all the solid that formed had dissolved. KNO3 (0.815 mL, 17.00 mmol) was added portionwise such that the temperature was maintained below 10° C. The mixture was stirred overnight and then poured onto ice/water. The mixture was basified with concentrated NH4OH. The resulting solid was filtered off and then dissolved in CH2Cl2, washed with water, dried (Na2SO4) and concentrated onto silica. Purification by FCC, eluting with 50-0% heptane in CH2Cl2 gave the title compound (2.450 g, 77%) as a yellow crystalline solid; 1H NMR: 3.91 (3H, s), 5.21 (2H, s), 7.03 (1H, d), 7.35 (1H, d); m/z: ES+ MH+ 187.4. ### ORD JSON:	{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "NH4OH"}], "reaction_role": "REACTANT"}]}, "m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-Fluoro-2-methoxyaniline"}], "amount": {"mass": {"value": 2.4, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "H2SO4"}], "amount": {"volume": {"value": 15.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "KNO3"}], "amount": {"volume": {"value": 0.815, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "The mixture was stirred until all the solid"}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "was cooled in a ice/water bath"}, {"type": "ADDITION", "details": "where the temperature was kept below 15\u00b0 C. during the addition"}, {"type": "CUSTOM", "details": "that formed"}, {"type": "DISSOLUTION", "details": "had dissolved"}, {"type": "TEMPERATURE", "details": "was maintained below 10\u00b0 C"}, {"type": "STIRRING", "details": "The mixture was stirred overnight", "duration": {"value": 8.0, "precision": 8.0, "units": "HOUR"}}, {"type": "ADDITION", "details": "poured onto ice/water"}, {"type": "FILTRATION", "details": "The resulting solid was filtered off"}, {"type": "DISSOLUTION", "details": "dissolved in CH2Cl2", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "CH2Cl2"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "washed with water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried (Na2SO4)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Na2SO4"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated onto silica"}, {"type": "CUSTOM", "details": "Purification by FCC"}, {"type": "WASH", "details": "eluting with 50-0% heptane in CH2Cl2", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "heptane"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "CH2Cl2"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 2.45, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 77.0}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 77.4}}], "isolated_color": "yellow 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. ### Procedure: A solution of 5-(2,6-difluoro-3-nitrophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole (1.23 g, 4 mmol) and N-bromosuccinimide (1.25 g, 7 mmol) in dichloromethane (10 mL) was stirred at room temperature for 18 h. The solution was washed with water, dried over anhydrous sodium sulfate and concentrated. Crude 4-bromo-5-(2,6-difluoro-3-nitrophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole was obtained. ### ORD JSON:	{"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "5-(2,6-difluoro-3-nitrophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole"}], "amount": {"mass": {"value": 1.23, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "N-bromosuccinimide"}], "amount": {"mass": {"value": 1.25, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "WASH", "details": "The solution was 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": "CONCENTRATION", "details": "concentrated"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "4-bromo-5-(2,6-difluoro-3-nitrophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole"}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 4-(Bromomethyl)benzenesulfonyl chloride (5.0 g, 18.6 mmol) was dissolved in tetrahydrofuran. Ethanolamine (1.1 mL, 18.6 mmol) and N,N-diisopropylethylamine (3.9 mL, 22.3 mmol) were added, and the reaction was allowed to stir at ambient temperature for 30 minutes. The reaction was concentrated to an oil that was partitioned between water and ethyl acetate and extracted with ethyl acetate. The organic extracts were combined, washed with brine, dried over Na2SO4, and filtered. The resulting filtrate was concentrated to an oil that was a mixture of the title compound and 4-chloromethyl N-(2-hydroxyethyl)benzenesulfonamide. The resulting oil was dried in vacuo (3.7 g, 68%). ES-MS m/z 250 (M+H) and 294 (M+H). ### ORD JSON:	{"inputs": {"m1_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(Bromomethyl)benzenesulfonyl chloride"}], "amount": {"mass": {"value": 5.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tetrahydrofuran"}], "reaction_role": "SOLVENT"}]}, "m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "Ethanolamine"}], "amount": {"volume": {"value": 1.1, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "N,N-diisopropylethylamine"}], "amount": {"volume": {"value": 3.9, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "to stir at ambient temperature for 30 minutes"}, "conditions_are_dynamic": true}, "workups": [{"type": "CONCENTRATION", "details": "The reaction was concentrated to an oil that"}, {"type": "CUSTOM", "details": "was partitioned between water and ethyl acetate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}]}}, {"type": "EXTRACTION", "details": "extracted with ethyl acetate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "washed with brine", "input": {"components": [{"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": "FILTRATION", "details": "filtered"}, {"type": "CONCENTRATION", "details": "The resulting filtrate was concentrated to an oil that"}, {"type": "ADDITION", "details": "a mixture of the title compound and 4-chloromethyl N-(2-hydroxyethyl)benzenesulfonamide", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "4-chloromethyl N-(2-hydroxyethyl)benzenesulfonamide"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "The resulting oil was dried in vacuo (3.7 g, 68%)"}], "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. ### Procedure: Adamantylamine (0.045 mole) and dimethyl (carboxymethyl)phosphonate (0.04 mole) were dissolved in 100 ml. of methylene chloride. As the solution was stirred, dicyclohexylcarbodiimide was added portionwise. The solution was stirred overnight, and the mixture filtered. The filtrate was concentrated to a solid. It was recrystallized from an appropriate solvent such as methanol. m.p. 190°-4° C.; yield, 32%. ### ORD JSON:	{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "methylene chloride"}], "reaction_role": "SOLVENT"}]}, "m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Adamantylamine"}], "amount": {"moles": {"value": 0.045, "units": "MOLE"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dimethyl (carboxymethyl)phosphonate"}], "amount": {"moles": {"value": 0.04, "units": "MOLE"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "dicyclohexylcarbodiimide"}], "reaction_role": "REACTANT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "As the solution was stirred"}, "conditions_are_dynamic": true}, "workups": [{"type": "STIRRING", "details": "The solution was stirred overnight", "duration": {"value": 8.0, "precision": 8.0, "units": "HOUR"}}, {"type": "FILTRATION", "details": "the mixture filtered"}, {"type": "CONCENTRATION", "details": "The filtrate was concentrated to a solid"}, {"type": "CUSTOM", "details": "It was recrystallized from an appropriate solvent such as methanol", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "methanol"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "yield"}], "outcomes": [{"products": [{}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A mixture of p-nitrobenzyl α-thioformamidodiphenylphosphonoacetate (2.43 g), powdered potassium carbonate (0.73 ), 1-chloro-3-methoxy-2-propanone (0.63 g), and acetone (25 ml) is stirred in a capped flask at room temperature for 16 hours. The mixture is filtered and the filtrate is evaporated in vacuo to afford 3-methoxy-2-oxopropyl N-(p-nitrobenzyloxycarbonyl-diphenylphosphonomethyl)thioformimidate. ### ORD JSON:	{"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "p-nitrobenzyl \u03b1-thioformamidodiphenylphosphonoacetate"}], "amount": {"mass": {"value": 2.43, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "potassium carbonate"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1-chloro-3-methoxy-2-propanone"}], "amount": {"mass": {"value": 0.63, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "acetone"}], "amount": {"volume": {"value": 25.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "is stirred in a capped flask at room temperature for 16 hours"}, "conditions_are_dynamic": true}, "workups": [{"type": "FILTRATION", "details": "The mixture is filtered"}, {"type": "CUSTOM", "details": "the filtrate is evaporated in vacuo"}], "outcomes": [{"reaction_time": {"value": 16.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "3-methoxy-2-oxopropyl N-(p-nitrobenzyloxycarbonyl-diphenylphosphonomethyl)thioformimidate"}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A flask was charged with 4-(tert-butyldimethylsilyloxy)-N-((6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methyl)butanethioamide (0.158 g, 0.241 mmol) and 1,4-dioxane (3 mL). To the mixture was added bis(2,2,2-trifluoroacetoxy)mercury (0.103 g, 0.241 mmol). The mixture was heated to about 65° C. for 1 h. The mixture was then filtered and concentrated under reduced pressure. The material was purified using silica gel chromatography with an elution gradient of 15 to 100% EtOAc/heptane followed by 0 to 5% MeOH/DCM to give 3-(7-(5-methoxy-1-methyl-1H-indol-3-yl)-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)propan-1-ol (0.022 g, 18%): LC/MS (Table 2, Method b) Rt=2.59 min; MS m/z 506 (M+H)+. ### ORD JSON:	{"inputs": {"m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(tert-butyldimethylsilyloxy)-N-((6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methyl)butanethioamide"}], "amount": {"mass": {"value": 0.158, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1,4-dioxane"}], "amount": {"volume": {"value": 3.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "bis(2,2,2-trifluoroacetoxy)mercury"}], "amount": {"mass": {"value": 0.103, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}}, "conditions": {"temperature": {"setpoint": {"value": 65.0, "units": "CELSIUS"}}, "conditions_are_dynamic": true}, "workups": [{"type": "FILTRATION", "details": "The mixture was then filtered"}, {"type": "CONCENTRATION", "details": "concentrated under reduced pressure"}, {"type": "CUSTOM", "details": "The material was purified"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "3-(7-(5-methoxy-1-methyl-1H-indol-3-yl)-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)propan-1-ol"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.022, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 18.0}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 18.1}}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To a 250 mL RBF containing tert-butyl (1S,2R)-1-fluoro-1-phenylbut-3-en-2-ylcarbamate (105.00 mg, 396 mmol)(mixture of diasteromers at benzylic fluoride stereocenter) was added tert-butanol (3 mL) and water (1 ml). The mixture was allowed to stir at 23° C. for 2 min, then NMO (139 mg, 1187 mmol) and osmium tetraxide (124 μA, 396 mmol) were added and the reaction was allowed to stir for another 48 h. before the reaction was quenched with water and sodium sulfite (1496 mg, 11872 mmol). The reaction was allowed to stir for 15 min and then extracted with EtOAc (3×). The combined organics were washed with HCl (1 N), sodium bicarbonate, brine and dried over sodium sulfate. The dried solution was passed through a plug of silica gel and concentrated to give 102 mg of a colorless oil ### ORD JSON:	{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "tert-butyl (1S,2R)-1-fluoro-1-phenylbut-3-en-2-ylcarbamate"}], "amount": {"mass": {"value": 105.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m3_m7": {"components": [{"identifiers": [{"type": "NAME", "value": "NMO"}], "amount": {"mass": {"value": 139.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "osmium"}], "reaction_role": "CATALYST"}]}, "m2_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "tert-butanol"}], "amount": {"volume": {"value": 3.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 1.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m5_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium sulfite"}], "amount": {"mass": {"value": 1496.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 23.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "to stir at 23\u00b0 C. for 2 min"}, "conditions_are_dynamic": true}, "workups": [{"type": "STIRRING", "details": "to stir for another 48 h. before the reaction", "duration": {"value": 48.0, "units": "HOUR"}}, {"type": "STIRRING", "details": "to stir for 15 min", "duration": {"value": 15.0, "units": "MINUTE"}}, {"type": "EXTRACTION", "details": "extracted with EtOAc (3\u00d7)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "EtOAc"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "The combined organics were washed with HCl (1 N), sodium bicarbonate, brine", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "HCl"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "sodium bicarbonate"}], "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"}], "outcomes": [{"reaction_time": {"value": 2.0, "units": "MINUTE"}, "products": [{"identifiers": [{"type": "NAME", "value": "colorless oil"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 102.0, "units": "MILLIGRAM"}}}], "isolated_color": "colorless", "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. ### Procedure: A mixture of (R)-4-(2-(2-methylpyrrolidin-1-yl)ethyl)phenylboronic acid hydrochloride (50 mg, 0.185 mmol), 5-(4-bromophenethyl)-1H-tetrazole (56.3 mg, 0.223 mmol), Na2CO3 (79 mg, 0.742 mmol), and dichlorobis(p-dimethylaminophenyldi-tert-butylphosphine)palladium (1.313 mg, 1.855 μmol) in 1,4-dioxane (1 mL) and H2O (0.2 mL) was heated under microwave irradiation at 130° C. for 120 min. The mixture was concentrated and the residue was purified by HPLC to give the title compound. LCMS m/z=362.5 [M+H]+; 1.22-1.31 (m, 0.4H), 1.45 (d, J=6.6 Hz, 2.6H), 1.69-1.82 (m, 1H), 2.00-2.10 (m, 2H), 2.21-2.32 (m, 1H), 3.04-3.20 (m, 6H), 3.25-3.31 (m, 2H), 3.35-3.47 (m, 1H), 3.50-3.60 (m, 1H), 3.72-3.83 (m, 1H), 7.31 (d, J=8.1 Hz, 2H), 7.37 (d, J=8.1 Hz, 2H), 7.56 (d, J=8.2 Hz, 2H), 7.61 (d, J=8.2 Hz, 2H). ### ORD JSON:	{"inputs": {"m1_m2_m3_m4_m5_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "(R)-4-(2-(2-methylpyrrolidin-1-yl)ethyl)phenylboronic acid hydrochloride"}], "amount": {"mass": {"value": 50.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "5-(4-bromophenethyl)-1H-tetrazole"}], "amount": {"mass": {"value": 56.3, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Na2CO3"}], "amount": {"mass": {"value": 79.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dichlorobis(p-dimethylaminophenyldi-tert-butylphosphine)palladium"}], "amount": {"mass": {"value": 1.313, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1,4-dioxane"}], "amount": {"volume": {"value": 1.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "H2O"}], "amount": {"volume": {"value": 0.2, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 130.0, "units": "CELSIUS"}}, "conditions_are_dynamic": true}, "workups": [{"type": "CONCENTRATION", "details": "The mixture was concentrated"}, {"type": "CUSTOM", "details": "the residue was purified by HPLC"}], "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. ### Procedure: 3.4 g (0.008 mol) of pentafluoropropionyl bromide 2,4,6-trichlorophenylhydrazone and 0.8 g (0.008 mol) of N,N-diethylcyanamide were added to 20 ml of toluene. Then, 0.9 g (0.009 mol) of triethylamine was added thereto under stirring at room temperature. After completion of the dropwise addition, stirring was continued at room temperature for further 1 hour. Then, 20 ml of toluene was added thereto, followed by washing with water. The organic layer was dried, and the solvent was distilled off. The residue was purified by silica gel column chromatography to obtain 1.9 g (yield: 54.3%) of the desired compound as a brown powder. Melting point: 66°-70° C. ### ORD JSON:	{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "toluene"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1_m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "pentafluoropropionyl bromide 2,4,6-trichlorophenylhydrazone"}], "amount": {"mass": {"value": 3.4, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "N,N-diethylcyanamide"}], "amount": {"mass": {"value": 0.8, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "toluene"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "triethylamine"}], "amount": {"mass": {"value": 0.9, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "under stirring at room temperature"}, "conditions_are_dynamic": true}, "workups": [{"type": "ADDITION", "details": "After completion of the dropwise addition"}, {"type": "STIRRING", "details": "stirring"}, {"type": "WASH", "details": "by washing with water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "The organic layer was dried"}, {"type": "DISTILLATION", "details": "the solvent was distilled off"}, {"type": "CUSTOM", "details": "The residue was purified by silica gel column chromatography"}], "outcomes": [{"reaction_time": {"value": 1.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "desired compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 1.9, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 54.3}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 54.3}}], "isolated_color": "brown", "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. ### Procedure: To a solution of 4-(4-Bromo-thiazol-2-yl)-2-chloro-pyrimidine (25)(0.498 g, 1.8 mmol) in EtOH (8 ml) was added powdered potassium carbonate (0.274 g, 1.98 mmol) and morpholine (0.17 ml, 1.98 mmol). The mixture was heated under the influence of microwave radiation (10 minutes, 90° C., high absorption setting). The reaction mixture was then allowed to cool to room temperature and filtered through a thin pad of silica before being concentrated in vacuo. The crude residue was purified by flash chromatography (SiO2) using Hexanes:EtOAc—(9:1) as eluent to give the title compound (0.18 g, 30.5%) in analytically pure form. m/z (LC-MS, ESP): 327 [M+H]+, R/T=3.92 mins. ### ORD JSON:	{"inputs": {"m1_m4_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(4-Bromo-thiazol-2-yl)-2-chloro-pyrimidine"}], "amount": {"mass": {"value": 0.498, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "potassium carbonate"}], "amount": {"mass": {"value": 0.274, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "morpholine"}], "amount": {"volume": {"value": 0.17, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "EtOH"}], "amount": {"volume": {"value": 8.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 90.0, "units": "CELSIUS"}}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "to cool to room temperature", "temperature": {"control": {"type": "AMBIENT"}}}, {"type": "FILTRATION", "details": "filtered through a thin pad of silica"}, {"type": "CONCENTRATION", "details": "before being concentrated in vacuo"}, {"type": "CUSTOM", "details": "The crude residue was purified by flash chromatography (SiO2)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "crude residue"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.18, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 30.5}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 30.6}}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: Following the procedure described in Japanese Patent Publication 39272/74, 50.0 ml of water was cooled to 3° C. and slowly 18.4 g (0.1 mole) of cyanuric chloride was added while maintaining 3°-5° C. by means of an external ice-water bath. Slowly 26.0 g (0.2 mole) of 3-(diethylamino)propylamine was added while maintaining 3°-12° C. by means of an ice-water bath. The resulting solution was stirred at ambient temperature for approximately eight hours and allowed to stand overnight. Slowly a 10 percent aqueous potassium carbonate solution was added to the reaction solution until it was slightly alkaline. The solid which precipitated was collected by filtration. The water wet filter cake was resuspended in water and dissolved by the addition of hydrochloric acid. Slowly 10 percent aqueous potassium carbonate was added until the mixture was slightly alkaline. The resulting solid was collected by filtration, washed with water and dried in vacuo to obtain 2-chloro-4,6-bis[3-(diethylamino)-propyl]amino-1,3,5-triazine, a water-insoluble, white colored solid which melted at 119° C. ### ORD JSON:	{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "cyanuric chloride"}], "amount": {"mass": {"value": 18.4, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "3-(diethylamino)propylamine"}], "amount": {"mass": {"value": 26.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "potassium carbonate"}], "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 3.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "The resulting solution was stirred at ambient temperature for approximately eight hours"}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "while maintaining 3\u00b0-5\u00b0 C. by means of an external ice-water bath"}, {"type": "TEMPERATURE", "details": "while maintaining 3\u00b0-12\u00b0 C. by means of an ice-water bath"}, {"type": "WAIT", "details": "to stand overnight", "duration": {"value": 8.0, "precision": 8.0, "units": "HOUR"}}, {"type": "CUSTOM", "details": "The solid which precipitated"}, {"type": "FILTRATION", "details": "was collected by filtration"}, {"type": "DISSOLUTION", "details": "dissolved by the addition of hydrochloric acid", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "reaction_role": "WORKUP"}]}}, {"type": "ADDITION", "details": "Slowly 10 percent aqueous potassium carbonate was added until the mixture", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "potassium carbonate"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "The resulting solid was collected by filtration"}, {"type": "WASH", "details": "washed with water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "dried in vacuo"}], "outcomes": [{"reaction_time": {"value": 8.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "2-chloro-4,6-bis[3-(diethylamino)-propyl]amino-1,3,5-triazine"}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: The compound was prepared based on the methodology in Example 5 using 38 mg (0.15 mmol) of 5-(4-hydroxy-3,5-dimethoxyphenyl)-penta-2E,4E-dienoic acid [Example 4], 67 mg (0.30 mmol) of 3,4 dihydroxybenzylamine hydrobromide, 153 μl (1.5 mmol) of triethylamine, and 100 mg (0.23 mmol) of BOP reagent. ### ORD JSON:	{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "BOP reagent"}], "amount": {"mass": {"value": 100.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "5-(4-hydroxy-3,5-dimethoxyphenyl)-penta-2E,4E-dienoic acid"}], "amount": {"mass": {"value": 38.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "3,4 dihydroxybenzylamine hydrobromide"}], "amount": {"mass": {"value": 67.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "triethylamine"}], "amount": {"volume": {"value": 153.0, "units": "MICROLITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The compound was prepared"}], "outcomes": [{"products": [{}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To a 20 mL scintillation vial was added the product from Example 26C (30 mg, 0.085 mmol), methyl 2-(methylamino)acetate (10.0 mg, 0.097 mmol), and N,N-dimethylformamide (0.85 mL) followed by O-(7-azabenzotriazol-1-yl)-N,N,N′N′-tetramethyluronium hexafluorophosphate (39.0 mg, 0.102 mmol) and diisopropylethylamine (30.0 μL, 0.176 mmol). Following 4 hours of stirring at room temperature, the solvent was evaporated and the residue purified over RP-HPLC to afford the title product. The NMR spectrum includes a mixture of rotamers, with the major rotamer being reported. 1H NMR (500 (MHz, DMSO-d6) δ ppm 0.98-1.20 (m, 2 H), 1.38-1.55 (m, 2 H), 1.70-1.93 (m, 5 H), 2.20-2.33 (m, 2 H), 2.78-2.88 (m, 1 H), 3.01-3.10 (m, 3 H), 3.64 (s, 3 H), 4.08 (s, 2 H), 7.03-7.19 (m, 1 H), 7.28-7.41 (m, 2 H), 7.66-7.76 (m, 2 H), 13.80-14.09 (m, 1 H); MS (ESI) m/z 438 [M+H]+. ### ORD JSON:	{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "diisopropylethylamine"}], "amount": {"volume": {"value": 30.0, "units": "MICROLITER"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "product"}], "amount": {"mass": {"value": 30.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methyl 2-(methylamino)acetate"}], "amount": {"mass": {"value": 10.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "N,N-dimethylformamide"}], "amount": {"volume": {"value": 0.85, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "O-(7-azabenzotriazol-1-yl)-N,N,N\u2032N\u2032-tetramethyluronium hexafluorophosphate"}], "amount": {"mass": {"value": 39.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "of stirring at room temperature"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "the solvent was evaporated"}, {"type": "CUSTOM", "details": "the residue purified over RP-HPLC"}], "outcomes": [{"reaction_time": {"value": 4.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "title product"}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 2-bromo-3-pyridinol (230 mg) and potassium carbonate (216 mg) was dissolved in methylethylketone (10 ml) and reacted for 30 minutes. Then, (S)-3-bromo-2-methyl-1-propanol (0.21 ml) was added to the solution and refluxed for 3 hours at 100° C. Potassium carbonate was filtered out and separated by flash chromatography under a silica gel phase (ethyl acetate:normal hexane=1:1). As a result, (S)-3-(2-bromopyridine-3-yloxy)-2-methyl-1-propanol (260 mg, yield: 80%) was obtained. ### ORD JSON:	{"inputs": {"m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "2-bromo-3-pyridinol"}], "amount": {"mass": {"value": 230.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "potassium carbonate"}], "amount": {"mass": {"value": 216.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methylethylketone"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "(S)-3-bromo-2-methyl-1-propanol"}], "amount": {"volume": {"value": 0.21, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 100.0, "units": "CELSIUS"}}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "reacted for 30 minutes", "duration": {"value": 30.0, "units": "MINUTE"}}, {"type": "FILTRATION", "details": "Potassium carbonate was filtered out", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Potassium carbonate"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "separated by flash chromatography under a silica gel phase (ethyl acetate:normal hexane=1:1)"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "(S)-3-(2-bromopyridine-3-yloxy)-2-methyl-1-propanol"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 260.0, "units": "MILLIGRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 80.0}}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A solution of 3H-thieno[3,2-d]pyrimid-4-one (3, 2.7 g, 18 mmol) in phosphorus oxychloride (18 mL) under N2 was heated at reflux for 1 hour. The resulting solution was allowed to cool to room temperature and then poured into a saturated aqueous solution of sodium bicarbonate to neutralize. The aqueous mixture was extracted with diethyl ether. The organic layer was washed with water followed by saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and the solvent evaporated under reduced pressure to yield 4-chlorothieno[3,2-d]pyrimidine (2.9 g, 97% yield) as a white solid. ### ORD JSON:	{"inputs": {"m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "3H-thieno[3,2-d]pyrimid-4-one"}], "amount": {"mass": {"value": 2.7, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "phosphorus oxychloride"}], "amount": {"volume": {"value": 18.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium bicarbonate"}], "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "at reflux for 1 hour", "duration": {"value": 1.0, "units": "HOUR"}}, {"type": "EXTRACTION", "details": "The aqueous mixture was extracted with diethyl ether", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "diethyl ether"}], "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": "dried over anhydrous magnesium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "magnesium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "the solvent evaporated under reduced pressure"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "4-chlorothieno[3,2-d]pyrimidine"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 2.9, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 97.0}}], "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. ### Procedure: To an ethanolic solution of sodium ethoxide, generated by portionwise addition of sodium metal (10.5 g, 455 mmol) to stirred ethanol (450 ml), was added N-[5-(2-chlorophenyl)-2H-pyrazol-3-yl]-acetamidine, acetate salt (I-1A-1b; 13.4 g, 45.5 mmol) in one portion. Diethylcarbonate (44.1 ml, 364 mmol) was added, dropwise, and the mixture was heated to reflux, overnight. After cooling to room temperature, the reaction was concentrated, in vacuo, and then extracted with ethyl acetate from water, adjusted to pH 6 with 3 M aqueous HCL. The combined organic layers were washed with brine, dried (MgSO4), filtered, and then concentrated, in vacuo, to afford the crude product as an off-white solid (11.0 g). The solids were triturated from ethyl acetate (100 ml), the supernate was decanted away, the solids were washed with additional ethyl acetate (100 ml) and then dried, in vacuo, to afford I-1A-1c as a colorless solid (10.0 g, 84%): +APcI MS (M+1) 261.2; 1H NMR (400 MHz, CD3OD) δ 7.84-7.81 (m, 1H), 7.54-7.51 (m, 1H), 7.44-7.38 (m, 2H), 6.77 (s, 1H), 2.42 (s, 3H). ### ORD JSON:	{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Diethylcarbonate"}], "amount": {"volume": {"value": 44.1, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium ethoxide"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium"}], "amount": {"mass": {"value": 10.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"volume": {"value": 450.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "N-[5-(2-chlorophenyl)-2H-pyrazol-3-yl]-acetamidine, acetate salt"}], "amount": {"mass": {"value": 13.4, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "dropwise, and the mixture was heated"}, {"type": "TEMPERATURE", "details": "to reflux, overnight", "duration": {"value": 8.0, "precision": 8.0, "units": "HOUR"}}, {"type": "CONCENTRATION", "details": "the reaction was concentrated, in vacuo"}, {"type": "EXTRACTION", "details": "extracted with ethyl acetate from water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "water"}], "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 (MgSO4)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "MgSO4"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CONCENTRATION", "details": "concentrated, in vacuo"}, {"type": "CUSTOM", "details": "to afford the crude product as an off-white solid (11.0 g)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "crude product"}], "amount": {"mass": {"value": 11.0, "units": "GRAM"}}, "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "The solids were triturated from ethyl acetate (100 ml)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "the supernate was decanted away"}, {"type": "WASH", "details": "the solids were washed with additional ethyl acetate (100 ml)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "dried, in vacuo"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "solid"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 10.0, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 84.0}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 84.3}}], "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. ### Procedure: To a mixture of methyl 1-butyl-4-iodo-1H-indole-6-carboxylate (Example SP-218, Step 4) (1.47 g) in N-methyl pyrrolidinone (15 mL) was added copper (I) cyanide (1.1 g). The mixture was heated to 150° C. for 6 h, removed from heat and cooled to room temperature. The mixture was partitioned between water and ethyl acetate and the layers were separated. The organic layer was washed three times with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Column chromatography on silica gel (100 mL) using 20% ethyl acetate as eluent to give 0.5 g of the title compound: 1H NMR (CDCl3) δ 0.955, 1.32, 1.85, 3.98, 4.23, 6.76, 7.43, 8.16, 8.30. ### ORD JSON:	{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl 1-butyl-4-iodo-1H-indole-6-carboxylate"}], "amount": {"mass": {"value": 1.47, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "copper (I) cyanide"}], "amount": {"mass": {"value": 1.1, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "N-methyl pyrrolidinone"}], "amount": {"volume": {"value": 15.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 150.0, "units": "CELSIUS"}}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "removed"}, {"type": "TEMPERATURE", "details": "from heat"}, {"type": "TEMPERATURE", "details": "cooled to room temperature", "temperature": {"control": {"type": "AMBIENT"}}}, {"type": "CUSTOM", "details": "The mixture was partitioned between water and ethyl acetate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "the layers were separated"}, {"type": "WASH", "details": "The organic layer was washed three times 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": "CONCENTRATION", "details": "concentrated under reduced pressure"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.5, "units": "GRAM"}}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 47.4}}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To the DMF solution of crude 5-hydroxymethylene-1-methyl-1,3a,5,6,7,7a-hexahydro-indazol-4-one was added 10 eq of N-(3-hydroxy-phenyl)-guanidine, the reaction mixture was stirred at 100° C. for overnight, LC/MS indicated one of the two peaks is the desired product. The DMF solution of reaction mixture was directly injected into prep HPLC, only a portion of the product mixture was purified. ### ORD JSON:	{"inputs": {"m3_m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "5-hydroxymethylene-1-methyl-1,3a,5,6,7,7a-hexahydro-indazol-4-one"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "N-(3-hydroxy-phenyl)-guanidine"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DMF"}], "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 100.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "the reaction mixture was stirred at 100\u00b0 C. for overnight"}, "conditions_are_dynamic": true}, "outcomes": [{"reaction_time": {"value": 8.0, "precision": 8.0, "units": "HOUR"}, "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. ### Procedure: N-methylmorpholine (15.25 ml) and ethyl chloroformate (12.60 ml) were added to a solution of (S)-2-((tert-butoxycarbonyl)amino)pent-4-enoic acid (25.0 g) in THF (250 ml) at −15° C. After stirring the mixture at −15° C. for 15 minutes, the generated insoluble matter was filtered off. A solution of sodium borohydride (3.23 g) in water (32 ml) was added to the filtrate at −15° C., and the mixture was stirred at −15° C. for 1 hour. A saturated aqueous ammonium chloride solution was added thereto, and the mixture was stirred at room temperature for 30 minutes. Ethyl acetate was added thereto to separate the organic layer. The organic layer was washed with a 0.5 N aqueous potassium hydrogensulfate solution, water, a 0.5 N aqueous sodium hydroxide solution, and a saturated sodium chloride solution; and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain the title compound as a light-yellow, oily substance (11.93 g). ### ORD JSON:	{"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "N-methylmorpholine"}], "amount": {"volume": {"value": 15.25, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethyl chloroformate"}], "amount": {"volume": {"value": 12.6, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "(S)-2-((tert-butoxycarbonyl)amino)pent-4-enoic acid"}], "amount": {"mass": {"value": 25.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "THF"}], "amount": {"volume": {"value": 250.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": -15.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "After stirring the mixture at \u221215\u00b0 C. for 15 minutes"}, "conditions_are_dynamic": true}, "workups": [{"type": "FILTRATION", "details": "the generated insoluble matter was filtered off"}, {"type": "ADDITION", "details": "A solution of sodium borohydride (3.23 g) in water (32 ml) was added to the filtrate at \u221215\u00b0 C.", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium borohydride"}], "amount": {"mass": {"value": 3.23, "units": "GRAM"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 32.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}, "temperature": {"setpoint": {"value": -15.0, "units": "CELSIUS"}}}, {"type": "STIRRING", "details": "the mixture was stirred at \u221215\u00b0 C. for 1 hour", "duration": {"value": 1.0, "units": "HOUR"}, "temperature": {"setpoint": {"value": -15.0, "units": "CELSIUS"}}}, {"type": "ADDITION", "details": "A saturated aqueous ammonium chloride solution was added", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ammonium chloride"}], "reaction_role": "WORKUP"}]}}, {"type": "STIRRING", "details": "the mixture was stirred at room temperature for 30 minutes", "duration": {"value": 30.0, "units": "MINUTE"}, "temperature": {"control": {"type": "AMBIENT"}}}, {"type": "ADDITION", "details": "Ethyl acetate was added", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Ethyl acetate"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "to separate the organic layer"}, {"type": "WASH", "details": "The organic layer was washed with a 0.5 N aqueous potassium hydrogensulfate solution, water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "potassium hydrogensulfate"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "and dried over anhydrous sodium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "DISTILLATION", "details": "The solvent was then distilled off under reduced pressure"}, {"type": "CUSTOM", "details": "The resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "hexane ethyl acetate"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 15.0, "units": "MINUTE"}, "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. ### Procedure: 5-Fluoro-1-(3-hydroxybenzenesulfonyl) indole was treated in a similar procedure as given in the Example 1 with 3-dimethylaminopropylchloride hydrochloride (2.48 mmol, 0.393 grams), with some non-critical variations to obtain the above derivative. ### ORD JSON:	{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "5-Fluoro-1-(3-hydroxybenzenesulfonyl) indole"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "3-dimethylaminopropylchloride hydrochloride"}], "amount": {"mass": {"value": 0.393, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "to obtain the above derivative"}], "outcomes": [{"products": [{}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 2,2,2-Trifluoroacetic acid (0.7 mL, 9.09 mmol) was added dropwise to tert-butyl 4-((5-(6-(bis(4-methoxybenzyl)amino)-2-methylpyrimidin-4-yl)-6-fluoropyridin-3-yl)methyl)piperazine-1-carboxylate (64.3 mg, 0.100 mmol) in dichloromethane (1.0 mL) at 25° C., and the resulting solution was stirred at 25° C. for 30 min. The reaction mixture was then concentrated in vacuo, and the residue was taken up in DCM (3.0 mL) and cooled to 0° C. Triethylamine (0.105 mL, 0.750 mmol) was added to the resulting solution, immediately followed by methanesulfonyl chloride (0.015 mL, 0.200 mmol). The resulting mixture was stirred at 0° C. for 20 min and then was concentrated onto silica gel and chromatographically purified (ISCO, 4 g, 0 to100% (10% MeOH-EtOAc)/hexanes) to provide 6-(2-fluoro-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-2-methylpyrimidin-4-amine (54.5 mg, 0.088 mmol, 88% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 8.45 (d, J=9.39 Hz, 1H); 8.14 (s, 1H); 7.17 (d, J=6.85 Hz, 4H); 6.86 (d, J=8.80 Hz, 5H); 4.74 (br. s., 4H); 3.79 (s, 6H); 3.60 (s, 2H); 3.25 (br. s., 4H); 2.78 (s, 3H); 2.62 (s, 3H); 2.58 (br. s., 4H). 19F NMR (377 MHz, CDCl3) 6-70.62 (d, J=8.01 Hz, 1 F). m/z (ESI, +ve ion) 621.1 (M+H)+. ### ORD JSON:	{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "methanesulfonyl chloride"}], "amount": {"volume": {"value": 0.015, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "2,2,2-Trifluoroacetic acid"}], "amount": {"volume": {"value": 0.7, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tert-butyl 4-((5-(6-(bis(4-methoxybenzyl)amino)-2-methylpyrimidin-4-yl)-6-fluoropyridin-3-yl)methyl)piperazine-1-carboxylate"}], "amount": {"mass": {"value": 64.3, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 1.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "Triethylamine"}], "amount": {"volume": {"value": 0.105, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 25.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "the resulting solution was stirred at 25\u00b0 C. for 30 min"}, "conditions_are_dynamic": true}, "workups": [{"type": "CONCENTRATION", "details": "The reaction mixture was then concentrated in vacuo"}, {"type": "TEMPERATURE", "details": "cooled to 0\u00b0 C", "temperature": {"setpoint": {"value": 0.0, "units": "CELSIUS"}}}, {"type": "STIRRING", "details": "The resulting mixture was stirred at 0\u00b0 C. for 20 min", "duration": {"value": 20.0, "units": "MINUTE"}, "temperature": {"setpoint": {"value": 0.0, "units": "CELSIUS"}}}, {"type": "CONCENTRATION", "details": "was concentrated onto silica gel"}, {"type": "CUSTOM", "details": "chromatographically purified (ISCO, 4 g, 0 to100% (10% MeOH-EtOAc)/hexanes)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "MeOH EtOAc"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "hexanes"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 30.0, "units": "MINUTE"}, "products": [{"identifiers": [{"type": "NAME", "value": "6-(2-fluoro-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-2-methylpyrimidin-4-amine"}], "measurements": [{"type": "AMOUNT", "details": "AMOUNT", "amount": {"moles": {"value": 0.088, "units": "MILLIMOLE"}}}, {"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 54.5, "units": "MILLIGRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 88.0}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 88.0}}], "isolated_color": "colorless", "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. ### Procedure: To a solution of 5-bromo-2-chlorobenzenemethanamine (i.e. the product of Synthesis Example 2, Step A) (1.3 g, 5.5 mmol) in dichloromethane (25 mL) at 0° C. was added carbonyl diimidazole (1.4 g, 8.6 mmol). The reaction mixture was stirred at room temperature for 1 h. Then the reaction mixture was cooled to 0° C., a solution of methylamine in THF (2 M, 3.0 mL, 6.0 mmol) was added, and the reaction mixture was stirred at room temperature for 4 h. The reaction mixture was filtered, and the solid residue was washed with pentane to provide the title product (1.0 g). ### ORD JSON:	{"inputs": {"m2": {"components": [{"identifiers": [{"type": "NAME", "value": "carbonyl diimidazole"}], "amount": {"mass": {"value": 1.4, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m1_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "5-bromo-2-chlorobenzenemethanamine"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 25.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "methylamine"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "THF"}], "amount": {"volume": {"value": 3.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "The reaction mixture was stirred at room temperature for 1 h"}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "Then the reaction mixture was cooled to 0\u00b0 C.", "temperature": {"setpoint": {"value": 0.0, "units": "CELSIUS"}}}, {"type": "STIRRING", "details": "the reaction mixture was stirred at room temperature for 4 h", "duration": {"value": 4.0, "units": "HOUR"}, "temperature": {"control": {"type": "AMBIENT"}}}, {"type": "FILTRATION", "details": "The reaction mixture was filtered"}, {"type": "WASH", "details": "the solid residue was washed with pentane", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "pentane"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 1.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "title product"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 1.0, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: In a 100 mL round-bottomed flask, 1-acetyl-6-bromo-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile (250 mg, 947 μmol, Eq: 1.00), triethylamine (575 mg, 792 μl, 5.68 mmol, Eq: 6) and X-PHOS (181 mg, 379 μmol, Eq: 0.40) were combined with dioxane (25.0 ml) to give a colorless solution. [1,1′-bis(diphenylphosphino)ferrocene]dichloropaladium(II) (173 mg, 237 μmol, Eq: 0.25) and 2-fluorophenylboronic acid (265 mg, 1.89 mmol) were added and the resultant mixture was degassed for 5 minutes under Nitrogen. The reaction mixture was heated to 100° C. and microwaved for 1 hr. The reaction mixture was poured into 50 mL EtOAc and washed with H2O. The organic layers were dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 40 g, 20% to 30% EtOAc in hexanes) to give 6-(2-fluorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile (220 mg, 98%). ### ORD JSON:	{"inputs": {"m1_m2_m3_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "1-acetyl-6-bromo-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile"}], "amount": {"mass": {"value": 250.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "triethylamine"}], "amount": {"volume": {"value": 792.0, "units": "MICROLITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "X-PHOS"}], "amount": {"mass": {"value": 181.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dioxane"}], "amount": {"volume": {"value": 25.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "[1,1\u2032-bis(diphenylphosphino)ferrocene]dichloropaladium(II)"}], "amount": {"mass": {"value": 173.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-fluorophenylboronic acid"}], "amount": {"mass": {"value": 265.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 100.0, "units": "CELSIUS"}}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "to give a colorless solution"}, {"type": "CUSTOM", "details": "the resultant mixture was degassed for 5 minutes under Nitrogen", "duration": {"value": 5.0, "units": "MINUTE"}, "input": {"components": [{"identifiers": [{"type": "NAME", "value": "resultant mixture"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "microwaved for 1 hr", "duration": {"value": 1.0, "units": "HOUR"}}, {"type": "ADDITION", "details": "The reaction mixture was poured into 50 mL EtOAc", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "EtOAc"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "washed with H2O", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "H2O"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "The organic layers were dried over MgSO4", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "MgSO4"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated in vacuo"}, {"type": "CUSTOM", "details": "The crude material was purified by flash chromatography (silica gel, 40 g, 20% to 30% EtOAc in hexanes)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "crude material"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "EtOAc"}], "amount": {"mass": {"value": 40.0, "units": "GRAM"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "hexanes"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "6-(2-fluorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 220.0, "units": "MILLIGRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 98.0}}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: Solutions of 375 ml (325 g, 2.8 moles) of isoamyl nitrite, and of 378 grams (2.0 moles) of crude 4-bromo-2-fluoroaniline in 250 ml benzene are added separately and simultaneously dropwise over about 20 hours to 3500 ml of benzene vigorously stirred under a nitrogen atmosphere, and kept in a water bath at 65° C. The mixture is kept overnight at 65° C., then cooled, washed twice with 250 ml of water and evaporated. The dark oily residue is dissolved in 750 ml methanol and 450 ml concentrated hydrochloric acid, and treated with 138 grams (2.1 moles) of granular zinc, added in small portions over about 6 hours. In order to complete this "reductive upgrading", the solution is treated with 54 grams (1.0 mole) of fine iron filings over 0.5 hours. Within one hour the color of the mixture is visibly lighter. The solution is diluted with one liter of water and one liter of Skellysolve B hexanes, and the liquids are decanted from the remaining metals. The aqueous phase is extracted twice with one liter of Skellysolve B hexanes and the one liter of water, one liter of 1 N NaOH, and one liter of water. The solution is then passed through anhydrous sodium sulfate and evaporated to provide 389 grams of 4-bromo-2-fluoro-biphenyl. ### ORD JSON:	{"inputs": {"m6_m7": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 1.0, "units": "LITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "Skellysolve B hexanes"}], "amount": {"volume": {"value": 1.0, "units": "LITER"}}, "reaction_role": "SOLVENT"}]}, "m5_m8": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "amount": {"volume": {"value": 450.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "zinc"}], "amount": {"mass": {"value": 138.0, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}, "m9": {"components": [{"identifiers": [{"type": "NAME", "value": "iron"}], "amount": {"mass": {"value": 54.0, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}, "m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "isoamyl nitrite"}], "amount": {"volume": {"value": 375.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4-bromo-2-fluoroaniline"}], "amount": {"mass": {"value": 378.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "benzene"}], "amount": {"volume": {"value": 250.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "benzene"}], "reaction_role": "REACTANT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "vigorously stirred under a nitrogen atmosphere"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "kept in a water bath at 65\u00b0 C", "temperature": {"setpoint": {"value": 65.0, "units": "CELSIUS"}}}, {"type": "TEMPERATURE", "details": "cooled"}, {"type": "WASH", "details": "washed twice with 250 ml of water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 250.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "evaporated"}, {"type": "DISSOLUTION", "details": "The dark oily residue is dissolved in 750 ml methanol", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "methanol"}], "amount": {"volume": {"value": 750.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "ADDITION", "details": "added in small portions over about 6 hours", "duration": {"value": 6.0, "units": "HOUR"}}, {"type": "WAIT", "details": "Within one hour the color of the mixture is visibly lighter", "duration": {"value": 1.0, "units": "HOUR"}}, {"type": "CUSTOM", "details": "the liquids are decanted from the remaining metals"}, {"type": "EXTRACTION", "details": "The aqueous phase is extracted twice with one liter of Skellysolve B hexanes", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Skellysolve B hexanes"}], "amount": {"volume": {"value": 1.0, "units": "LITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "evaporated"}], "outcomes": [{"reaction_time": {"value": 8.0, "precision": 8.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "4-bromo-2-fluoro-biphenyl"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 389.0, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A solution of methyl 2-(N′-(4-chlorophenyl)ureido)-3-phenylpropanoate (2.8 g) obtained in Example 1a) and 1 N sodium hydroxide (20 ml) in methanol (20 ml)-THF (10 ml) was mixed at room temperature for 15 hours, and the reaction solution was concentrated under reduced pressure. The solution was acidified by adding 1 N hydrochloric acid to the concentrated solution, and then extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound as colorless powder (2.6 g, 95%). ### ORD JSON:	{"inputs": {"m1_m2_m4_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl 2-(N\u2032-(4-chlorophenyl)ureido)-3-phenylpropanoate"}], "amount": {"mass": {"value": 2.8, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium hydroxide"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "THF"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methanol"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CONCENTRATION", "details": "the reaction solution was concentrated under reduced pressure"}, {"type": "ADDITION", "details": "by adding 1 N hydrochloric acid to the concentrated solution", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "reaction_role": "WORKUP"}]}}, {"type": "EXTRACTION", "details": "extracted with ethyl acetate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "The extract was washed with saturated brine", "input": {"components": [{"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": "DISTILLATION", "details": "The solvent was distilled off under reduced pressure"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 2.6, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 95.0}}], "isolated_color": "colorless", "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. ### Procedure: 2,3-Dihydro-6,7-methylenedioxy-1,4-benzodioxin-2-methanamine (2.3 g, 11 mmole), 5-(3-bromopropoxy)quinoline (2.54 g, 9.2 mmole), and diisopropylethylamine (2.6 g, 20 mmole) were combined in 100 ml of DMF and heated at 80° C. for 24 hours under a nitrogen atmosphere. The solvent was then removed in vacuum and replaced with 500 ml of dichloromethane. The mixture was washed with 250 ml each of saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, dried over sodium sulfate, filtered, and concentrated in vacuum. The residue was column chromatographed on 250 g of silica gel using 2% methanol/dichloromethane as eluant. The product-containing fractions were combined and concentrated in vacuum and the residue (2.0 g) recrystallized from 50 ml of ethanol with the addition of 6 ml of 4N isopropanolic HCl to give 1.4 g of the title compound as an orange solid dihydrochloride, one-quarter hydrate, m.p. 140°-145° C. ### ORD JSON:	{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "DMF"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2,3-Dihydro-6,7-methylenedioxy-1,4-benzodioxin-2-methanamine"}], "amount": {"mass": {"value": 2.3, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "5-(3-bromopropoxy)quinoline"}], "amount": {"mass": {"value": 2.54, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "diisopropylethylamine"}], "amount": {"mass": {"value": 2.6, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 80.0, "units": "CELSIUS"}}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The solvent was then removed in vacuum"}, {"type": "WASH", "details": "The mixture was washed with 250 ml each of saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium bicarbonate"}], "amount": {"volume": {"value": 250.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "sodium chloride"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over sodium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CONCENTRATION", "details": "concentrated in vacuum"}, {"type": "CUSTOM", "details": "chromatographed on 250 g of silica gel using 2% methanol/dichloromethane as eluant"}, {"type": "CONCENTRATION", "details": "concentrated in vacuum"}, {"type": "CUSTOM", "details": "the residue (2.0 g) recrystallized from 50 ml of ethanol with the addition of 6 ml of 4N isopropanolic HCl", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "residue"}], "amount": {"mass": {"value": 2.0, "units": "GRAM"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "HCl"}], "amount": {"volume": {"value": 6.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 1.4, "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. ### Procedure: The title compound was prepared following the method of Example 147 and using 1 mL of a stock solution of 0.6 g (1.8 mmol) of material from Example 50 and 15 μL (0.11 mmol) benzoyl chloride. NMR was consistent with the proposed compound. ### ORD JSON:	{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "stock solution"}], "amount": {"volume": {"value": 1.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "material"}], "amount": {"mass": {"value": 0.6, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "benzoyl chloride"}], "amount": {"volume": {"value": 15.0, "units": "MICROLITER"}}, "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. ### Procedure: A solution of N-methyl-N-(3-methylbenzofuran-2-ylmethyl)acrylamide (0.190 g, 0.637 mmol) in propionitrile (3 mL) and DMF (0.6 mL) was deoxygenated with Ar for 20 min. The solution was treated with diisopropylethylamine (0.34 mL, 1.97 mmol) and 7-bromo-2,2-dimethyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine (0.188 g, 0.828 mmol). The solution was deoxygenated with Ar for 20 min. Pd(OAc)2 (0.014 g, 0.078 mmol) and P(o-tol)3 (0.038 g, 0.15 mmol) were then added and the solution was deoxygenated again with Ar for 20 min. The mixture was heated to reflux for 2 h, then allowed to cool. The mixture was diluted with H2O (200 mL) and the resulting solution was washed with EtOAc (3×50 mL). The combined organic layers were washed with brine (2×30 mL), dried (Na2SO4) and concentrated to a dark green oil. Column chromatography (silica gel, CH2Cl2/MeOH, 100 to 98:2) gave the title compound (0.12 g, 52%) as a light yellow solid and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 7.83 (br s, 1H), 7.62-7.60 (m, 1H), 7.56-7.51 (m, 2H), 7.48-7.41 (m, 1H), 7.38-7.69 (m, 4H), 5.01-4.95 (m, 2H), 4.03 (s, 2H), 3.48 (s, 2H), 3.06-2.90 (m, 3H), 2.18 (s, 3H); MS (ESI) m/e 364 (M+H)+. ### ORD JSON:	{"inputs": {"m7_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "P(o-tol)3"}], "amount": {"mass": {"value": 0.038, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Pd(OAc)2"}], "amount": {"mass": {"value": 0.014, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}, "m1_m5_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "N-methyl-N-(3-methylbenzofuran-2-ylmethyl)acrylamide"}], "amount": {"mass": {"value": 0.19, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "propionitrile"}], "amount": {"volume": {"value": 3.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "DMF"}], "amount": {"volume": {"value": 0.6, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "diisopropylethylamine"}], "amount": {"volume": {"value": 0.34, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "7-bromo-2,2-dimethyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine"}], "amount": {"mass": {"value": 0.188, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The solution was deoxygenated with Ar for 20 min", "duration": {"value": 20.0, "units": "MINUTE"}}, {"type": "CUSTOM", "details": "the solution was deoxygenated again with Ar for 20 min", "duration": {"value": 20.0, "units": "MINUTE"}}, {"type": "TEMPERATURE", "details": "The mixture was heated"}, {"type": "TEMPERATURE", "details": "to reflux for 2 h", "duration": {"value": 2.0, "units": "HOUR"}}, {"type": "TEMPERATURE", "details": "to cool"}, {"type": "ADDITION", "details": "The mixture was diluted with H2O (200 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "H2O"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "the resulting solution was washed with EtOAc (3\u00d750 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "EtOAc"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "The combined organic layers were washed with brine (2\u00d730 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "brine"}], "amount": {"volume": {"value": 30.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried (Na2SO4)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Na2SO4"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated to a dark green oil"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.12, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 52.0}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 51.8}}], "isolated_color": "light yellow", "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. ### Procedure: A mixture of titantetraethoxide (11.03 g, 48.4 mmol), (S)-tert.-butylsulfinamide (3.52 g, 29 mmol) and 1-(6-Bromo-3-fluoro-4-triethylsilanyl-pyridin-2-yl)-3-methoxy-propan-1-one (9.1 g, 24.18 mmol) in THF (100 ml) was stirred at 60° C. under a nitrogen atmosphere for 34 hours. The cold reaction mixture was diluted with ethyl acetate and poured onto icecold brine (200 ml) with gentle stirring. The precipitate was filtered through a pad of hyflo and washed with ethyl acetate. The filtrate was diluted with ethyl acetate and washed with brine, dried over sodium sulfate, filtered and evaporated. The crude yellowish-brown oil (10.67 g) was chromatographed over silica gel (Redisep column 120 g, cyclohexane/ethyl acetate 95:5) to give the title compound as a yellow-orange oil. 7.51 g (63.5% yield). ### ORD JSON:	{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "SOLVENT"}]}, "m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "(S)-tert.-butylsulfinamide"}], "amount": {"mass": {"value": 3.52, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1-(6-Bromo-3-fluoro-4-triethylsilanyl-pyridin-2-yl)-3-methoxy-propan-1-one"}], "amount": {"mass": {"value": 9.1, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "THF"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "brine"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 60.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "was stirred at 60\u00b0 C. under a nitrogen atmosphere for 34 hours"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The cold reaction mixture"}, {"type": "FILTRATION", "details": "The precipitate was filtered through a pad of hyflo"}, {"type": "WASH", "details": "washed with ethyl acetate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}]}}, {"type": "ADDITION", "details": "The filtrate was diluted with ethyl acetate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "washed with brine", "input": {"components": [{"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": "FILTRATION", "details": "filtered"}, {"type": "CUSTOM", "details": "evaporated"}, {"type": "CUSTOM", "details": "The crude yellowish-brown oil (10.67 g) was chromatographed over silica gel (Redisep column 120 g, cyclohexane/ethyl acetate 95:5)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "crude yellowish-brown oil"}], "amount": {"mass": {"value": 10.67, "units": "GRAM"}}, "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 34.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 63.5}}], "isolated_color": "yellow-orange", "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. ### Procedure: 7-Fluoro-5-methyl-2-(methylamino)-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-131) (0.17 g, 0.60 mmol) was dissolved in dimethyl sulfoxide (5 ml), then triethylamine (0.17 ml, 1.23 mmol) and (3S)-3-methylaminopyrrolidine (0.16 ml, 1.26 mmol) were added, followed by stirring in a sealed tube at an external temperature of about 150° C. for 4 hours. This was diluted with dichloromethane, washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1 to 10:1), then diisopropyl ether was added, and the insoluble matter was collected by filtration to obtain a beige solid (68.3 mg, 27%). ### ORD JSON:	{"inputs": {"m1_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "7-Fluoro-5-methyl-2-(methylamino)-6-phenyl-1,3-benzoxazole-4-carbonitrile"}], "amount": {"mass": {"value": 0.17, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dimethyl sulfoxide"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "triethylamine"}], "amount": {"volume": {"value": 0.17, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "(3S)-3-methylaminopyrrolidine"}], "amount": {"volume": {"value": 0.16, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 150.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "by stirring in a sealed tube at an external temperature of about 150\u00b0 C. for 4 hours"}, "conditions_are_dynamic": true}, "workups": [{"type": "WASH", "details": "washed with water and 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": "CUSTOM", "details": "The solvent was evaporated away under reduced pressure"}, {"type": "CUSTOM", "details": "the resulting residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1 to 10:1)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "methanol"}], "reaction_role": "WORKUP"}]}}, {"type": "ADDITION", "details": "diisopropyl ether was added", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "diisopropyl ether"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "the insoluble matter was collected by filtration"}], "outcomes": [{"reaction_time": {"value": 4.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "solid"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 68.3, "units": "MILLIGRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 27.0}}], "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. ### Procedure: To a stirred solution of 0.40 g (1.3 mmols) of N-[2-(4-chlorophenyl)-1-(1,2,4-triazol-1-yl)-2-hexyl]formamide in 5mL of methylene chloride under nitrogen was added 0.45 mL (3.26 mmols) of triethylamine. To this mixture was added a slurry of 0.439 g (1.63 mmols) of 3-ethyl-2-chlorobenzoxazolium tetrafluoroborate. which was weighed out under a nitrogen atmosphere, in 5 mL of methylene chloride. The reaction mixture was then allowed to stir at room temperature for 12 hours. The reaction mixture was poured into ice water and extracted with ethyl acetate. The combined organic layers were washed once with 10% hydrochloric acid, brine, and dried over magnesium sutfate. Removal of solvents gave a crude oil which was purified by column chromatography (Merck 60 silica gel, ethyl acetate/hexane) to give 0.20 g (52%) of a clear, colorless oil. 1H-NMR 200 MHz (CDCl3, Me4Si) 0.8 (t, J=5 Hz, CH2 -CH3), 1.0-1.6 (m, 4H, 1.90-2.2 (m, 2H), 4.55 (ABq, J=16.8 Hz, JAB =15 Hz, CH2 -N), 7.2-7.5 (q, 4H, aromatic H), 7.9 (s CH=N), 8.0 ppm (s, CH=N). ### ORD JSON:	{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ice water"}], "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "methylene chloride"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1_m5_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "N-[2-(4-chlorophenyl)-1-(1,2,4-triazol-1-yl)-2-hexyl]formamide"}], "amount": {"mass": {"value": 0.4, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "triethylamine"}], "amount": {"volume": {"value": 0.45, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methylene chloride"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "3-ethyl-2-chlorobenzoxazolium tetrafluoroborate"}], "amount": {"mass": {"value": 0.439, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "to stir at room temperature for 12 hours"}, "conditions_are_dynamic": true}, "workups": [{"type": "EXTRACTION", "details": "extracted with ethyl acetate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "The combined organic layers were washed once with 10% hydrochloric acid, brine", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "brine"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over magnesium sutfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "magnesium"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "Removal of solvents"}, {"type": "CUSTOM", "details": "gave a crude oil which"}, {"type": "CUSTOM", "details": "was purified by column chromatography (Merck 60 silica gel, ethyl acetate/hexane)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate hexane"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "to give 0.20 g (52%) of a clear, colorless oil"}], "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. ### Procedure: The title compound was prepared following the same general protocol as described for the synthesis of the (S)-allyl 1-(2-chloro-5-((1-methoxy-1-oxopropan-2-yl)oxy)benzyl)-2,3-dimethyl-1H-indole-5-carboxylate (Step 3, Example 26), using the (S)-methyl 2-(5-(bromomethyl)-2-chlorophenoxy)propanoate instead of the (S)-methyl 2-(3-(bromomethyl)-4-chlorophenoxy)propanoate ESI-MS (m/z): 456 [M+1]+. ### ORD JSON:	{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "(S)-allyl 1-(2-chloro-5-((1-methoxy-1-oxopropan-2-yl)oxy)benzyl)-2,3-dimethyl-1H-indole-5-carboxylate"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "(S)-methyl 2-(5-(bromomethyl)-2-chlorophenoxy)propanoate"}], "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. ### Procedure: Propargylamine (24.79 g, 0.450 mole; Aldrich, 99%) was added dropwise over 1 h to methyl trifluoroacetate (69.19 g, 0.540 mole, 1.2 eq, Aldrich) at 0°. After stirring an additional hour at 0°, distillation though a 15 cm Vigreux column afforded 62.12 g (91%) of trifluoroacetamide 43 as a colorless liquid (bp 68.5°-69.5° at 11 torr). This material was homogeneous by NMR and GC and was used interchangeably with spectroscopically-identical material prepared by acylating propargylamine with trifluoroacetic acid anhydride. ### ORD JSON:	{"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Propargylamine"}], "amount": {"mass": {"value": 24.79, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methyl trifluoroacetate"}], "amount": {"mass": {"value": 69.19, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "After stirring an additional hour at 0\u00b0"}, "conditions_are_dynamic": true}, "workups": [{"type": "DISTILLATION", "details": "distillation though a 15 cm Vigreux column"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "trifluoroacetamide"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 62.12, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 91.0}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 91.4}}], "isolated_color": "colorless", "texture": {"type": "CUSTOM", "details": "liquid"}, "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To a solution of 3-hydroxy-N-methyl-benzamide (Step A, 700 mg, 4.6 mmol, 1.0 eq.) in anhydrous DMF (10 mL) was added NaH (200 mg, 5.1 mmol, 1.1 eq.). The reaction was stirred for 10 min. at RT after which 4-chloro-2-nitro-phenylamine (2.0 g, 11.6 mmol, 2.5 eq.) was added. The resulting mixture was heated to 80° C. for 4 h. The reaction was quenched with NaHCO3 (aq.), diluted with CH2Cl2 (50 mL), and washed with 1 N NaOH (25 mL). The organic layer was dried over MgSO4, filtered and concentrated. The crude was further purified by column chromatography (0-100% EtOAc in hexanes) to give pure 3-(4-amino-3-nitro-phenoxy)-N-methyl-benzamide. ### ORD JSON:	{"inputs": {"m1_m4_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "3-hydroxy-N-methyl-benzamide"}], "amount": {"mass": {"value": 700.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "NaH"}], "amount": {"mass": {"value": 200.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DMF"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "4-chloro-2-nitro-phenylamine"}], "amount": {"mass": {"value": 2.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 80.0, "units": "CELSIUS"}}, "conditions_are_dynamic": true}, "workups": [{"type": "ADDITION", "details": "was added"}, {"type": "CUSTOM", "details": "The reaction was quenched with NaHCO3 (aq.)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "NaHCO3"}], "reaction_role": "WORKUP"}]}}, {"type": "ADDITION", "details": "diluted with CH2Cl2 (50 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "CH2Cl2"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "washed with 1 N NaOH (25 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "NaOH"}], "amount": {"volume": {"value": 25.0, "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"}, {"type": "CUSTOM", "details": "The crude was further purified by column chromatography (0-100% EtOAc in hexanes)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "EtOAc"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "hexanes"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "3-(4-amino-3-nitro-phenoxy)-N-methyl-benzamide"}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: The mixture of 2.5 g of N-(4- nitro-o-tolyl)-4-methylsulfonylphthalimide, 0.1 g of palladium on carbon, 80 ml of dimethylformamide and 200 ml of ethyl acetate is hydrogenated at 2.7 atm. and room temperature until the hydrogen uptake ceases. It is filtered, the filtrate extracted with hydrochloric acid, washed with ethyl acetate, basified with sodium carbonate, reextracted with ethyl acetate, the organic solution washed with water, dried filtered and evaporated. The residue is triturated with ethyl acetate-diethyl ether, to yield the N-(4-amino-o-tolyl)-4-methylsulfonylphthalimide melting at 214°-220°. ### ORD JSON:	{"inputs": {"m1_m4_m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "N-(4- nitro-o-tolyl)-4-methylsulfonylphthalimide"}], "amount": {"mass": {"value": 2.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dimethylformamide"}], "amount": {"volume": {"value": 80.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "palladium on carbon"}], "amount": {"mass": {"value": 0.1, "units": "GRAM"}}, "reaction_role": "CATALYST"}, {"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrogen"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "FILTRATION", "details": "It is filtered"}, {"type": "EXTRACTION", "details": "the filtrate extracted with hydrochloric acid", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "washed with ethyl acetate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "the organic solution washed with water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "dried"}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CUSTOM", "details": "evaporated"}, {"type": "CUSTOM", "details": "The residue is triturated with ethyl acetate-diethyl ether", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate diethyl ether"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "N-(4-amino-o-tolyl)-4-methylsulfonylphthalimide"}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A suspension of 4.35 g (0.01 mol) of 7β-amino-3-[1-(2methanesulfonamidoethyl)tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid in 50 ml of dry dimethylformamide is treated with 2 ml of triethylamine and the mixture is stirred for 15 minutes at 25°. A slight excess of 0.01 mol of the activated ester of 2,2,2-trifluoroethylsulfinylacetic acid is added to the mixture and it is stirred an additional hour. The reaction mixture is evaporated to dryness and water and ethyl acetate are added to the residue. The layers are separated, the ethyl acetate layer is discarded, fresh ethyl acetate is added to the aqueous phase and it is acidified to pH 2.5 by addition of 6N hydrochloric acid. The mixture is filtered, the layers are separated and the aqueous phase is extracted with ethyl acetate. The combined extracts are washed with water, dried (MgSO4) and evaporated to dryness to give the title compound. ### ORD JSON:	{"inputs": {"m2": {"components": [{"identifiers": [{"type": "NAME", "value": "triethylamine"}], "amount": {"volume": {"value": 2.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "7\u03b2-amino-3-[1-(2methanesulfonamidoethyl)tetrazol-5-ylthiomethyl]-3-cephem-4-carboxylic acid"}], "amount": {"mass": {"value": 4.35, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dimethylformamide"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ester"}], "amount": {"moles": {"value": 0.01, "units": "MOLE"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2,2,2-trifluoroethylsulfinylacetic acid"}], "reaction_role": "REACTANT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "the mixture is stirred for 15 minutes at 25\u00b0"}, "conditions_are_dynamic": true}, "workups": [{"type": "STIRRING", "details": "is stirred an additional hour"}, {"type": "CUSTOM", "details": "The reaction mixture is evaporated to dryness and water and ethyl acetate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}]}}, {"type": "ADDITION", "details": "are added to the residue"}, {"type": "CUSTOM", "details": "The layers are separated"}, {"type": "ADDITION", "details": "fresh ethyl acetate is added to the aqueous phase and it", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}]}}, {"type": "ADDITION", "details": "is acidified to pH 2.5 by addition of 6N hydrochloric acid", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "The mixture is filtered"}, {"type": "CUSTOM", "details": "the layers are separated"}, {"type": "EXTRACTION", "details": "the aqueous phase is extracted with ethyl acetate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "The combined extracts are washed with water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried (MgSO4)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "MgSO4"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "evaporated to dryness"}], "outcomes": [{"reaction_time": {"value": 15.0, "units": "MINUTE"}, "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. ### Procedure: To a solution of 1-(5-(tert-butyl)-2-(methoxymethoxy)-3-(6-(trifluoromethyl)pyridin-3-yl)phenyl)ethan-1-ol (529 mg, 1.38 mmol) and sodium bicarbonate (1.16 g, 13.8 mmol) in methylene chloride (40 mL) was added Dess Martin periodinane (3.00 g, 6.90 mmol) and the reaction stirred for 1 hour. The reaction mixture was poured onto a 1:1 mixture of saturated aqueous sodium sulfite solution (50 mL) and water (50 mL). The resulting mixture was extracted with ethyl acetate (150 mL). The organic phase was washed with 1 N aqueous sodium hydroxide solution (50 mL), and water (50 mL), an emulsion formed and saturated brine (100 mL) was added to separate layers. The organic phase was dried (MgSO4), filtered and the solvent removed under reduced pressure. The residue was purified using flash chromatography on silica eluting with a solvent gradient of 0 to 100% ethyl acetate in hexanes to give 1-(5-(tert-butyl)-2-(methoxymethoxy)-3-(6-(trifluoromethyl)pyridin-3-yl)phenyl)ethan-1-one (526 mg, 100% yield) as a white solid. ### ORD JSON:	{"inputs": {"m1_m2_m5_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "1-(5-(tert-butyl)-2-(methoxymethoxy)-3-(6-(trifluoromethyl)pyridin-3-yl)phenyl)ethan-1-ol"}], "amount": {"mass": {"value": 529.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium bicarbonate"}], "amount": {"mass": {"value": 1.16, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Dess Martin periodinane"}], "amount": {"mass": {"value": 3.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methylene chloride"}], "amount": {"volume": {"value": 40.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "brine"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m4_m7": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium sulfite"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "the reaction stirred for 1 hour"}, "conditions_are_dynamic": true}, "workups": [{"type": "EXTRACTION", "details": "The resulting mixture was extracted with ethyl acetate (150 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "amount": {"volume": {"value": 150.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "The organic phase was washed with 1 N aqueous sodium hydroxide solution (50 mL), and water (50 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium hydroxide"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "an emulsion formed"}, {"type": "CUSTOM", "details": "to separate layers"}, {"type": "DRY_WITH_MATERIAL", "details": "The organic phase was dried (MgSO4)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "MgSO4"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CUSTOM", "details": "the solvent removed under reduced pressure"}, {"type": "CUSTOM", "details": "The residue was purified"}], "outcomes": [{"reaction_time": {"value": 1.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "1-(5-(tert-butyl)-2-(methoxymethoxy)-3-(6-(trifluoromethyl)pyridin-3-yl)phenyl)ethan-1-one"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 526.0, "units": "MILLIGRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 100.0}}], "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. ### Procedure: To a stirred solution of ethyl 5-fluoro-1-isopropyl-1H-indazole-3-carboxylate (125 mg, 0.5 mmol, step 1 of Example 11) in tetrahydrofuran (8 mL) was added 1N aqueous sodium hydroxide solution (1.0 mL, 1.0 mmol) at room temperature. The resulting mixture was stirred at 60° C. for 20 h. The mixture was acidified with 2 N hydrochloric acid (1 mL) and extracted with ethyl acetate (50 mL×3). The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure to give 106 mg (95%) of the title compound as a white amorphous solid. ### ORD JSON:	{"inputs": {"m1_m4_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl 5-fluoro-1-isopropyl-1H-indazole-3-carboxylate"}], "amount": {"mass": {"value": 125.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium hydroxide"}], "amount": {"volume": {"value": 1.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tetrahydrofuran"}], "amount": {"volume": {"value": 8.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "amount": {"volume": {"value": 1.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 60.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "The resulting mixture was stirred at 60\u00b0 C. for 20 h"}, "conditions_are_dynamic": true}, "workups": [{"type": "EXTRACTION", "details": "extracted with ethyl acetate (50 mL\u00d73)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "The combined organic layer was dried over sodium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated under reduced pressure"}], "outcomes": [{"reaction_time": {"value": 20.0, "units": "HOUR"}, "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": 95.0}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 95.4}}], "isolated_color": "white amorphous", "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. ### Procedure: To a solution 3-Bromo-8-chloro-5,10-dihydro-indeno[1,2-b]indole (4.2 g, 13 mmol) in chloroform (150 mL) and 5% aqueous NaHCO3 (56 mL) was added mCPBA (7.5 g, 43 mmol) in chloroform (150 mL) dropwise over 30 minutes. The reaction mixture was stirred at room temperature for 2 hours and the layers were separated. The organic layer was washed with saturated aqueous NaHCO3, dried (Na2SO4), filtered and concentrated. The resulting oil was triturated with ether and filtered. The filter cake was washed with ether and dried in vacuo to give 8-Bromo-2-chloro-5H,11H-dibenzo[b,f]azocine-6-12-dione (2.0 g, 43%). 1HNMR (CDCl3) δ 7.67 (d, 1H, J+2.20 Hz), 7.59 (d, 1H, J=1.76 Hz), 7.42 (dd, 1H, J=7.92, 1.76 Hz), 7.32 (dd, 1H, J=8.01, 2.20 Hz), 7.02 (m, 2H), 4.44 (d, 1H, J=15.40 Hz), 3.85 (d, 1H, J=14.96 Hz). HPLC Rt=3.65 min. ### ORD JSON:	{"inputs": {"m1_m4_m3_m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "3-Bromo-8-chloro-5,10-dihydro-indeno[1,2-b]indole"}], "amount": {"mass": {"value": 4.2, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "mCPBA"}], "amount": {"mass": {"value": 7.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "NaHCO3"}], "amount": {"volume": {"value": 56.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "chloroform"}], "amount": {"volume": {"value": 150.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "chloroform"}], "amount": {"volume": {"value": 150.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "The reaction mixture was stirred at room temperature for 2 hours"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "the layers were separated"}, {"type": "WASH", "details": "The organic layer was washed with saturated aqueous NaHCO3", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "NaHCO3"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried (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 triturated with ether", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ether"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "WASH", "details": "The filter cake was washed with ether", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ether"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "dried in vacuo"}], "outcomes": [{"reaction_time": {"value": 2.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "8-Bromo-2-chloro-5H,11H-dibenzo[b,f]azocine-6-12-dione"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 2.0, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 43.0}}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 4-Hydroxy-2-(4-iodophenyl)-2H-phthalazin-1-one (see Method Q) (0.30 g, 0.8 mmol), sodium 2-methyl-propane-2-thiolate (0.094 g, 0.8 mmol), CuI (0.011 g, 0.06 mmol) and ethylene glycol (0.10 g, 1.6 mmol) were dissolved in N-methyl-pyrrolidinone (NMP) (0.5 ml) under argon and heated to 150° C. Stirring at this temperature was continued for 4 d before the mixture was allowed to warm to room temperature. H2O (50 ml) was added and the precipitated solid was collected by filtration. The title compound was obtained after purification of the raw product by chromatography over silica gel with dichloromethane (0.21 g, 78%). 1H-NMR: (400 MHz, D6-DMSO) 12.35 (1H, s), 8.73 (1H, d), 8.33–8.41 (3H, m), 8.14 (2H, d), 8.01 (2H, d), 1.70 (9H, s); MS (ESI+)=327.14 (M+H)+. ### ORD JSON:	{"inputs": {"m1_m2_m6_m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "4-Hydroxy-2-(4-iodophenyl)-2H-phthalazin-1-one"}], "amount": {"mass": {"value": 0.3, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium 2-methyl-propane-2-thiolate"}], "amount": {"mass": {"value": 0.094, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethylene glycol"}], "amount": {"mass": {"value": 0.1, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "N-methyl-pyrrolidinone"}], "amount": {"volume": {"value": 0.5, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "CuI"}], "amount": {"mass": {"value": 0.011, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}, "m4": {"components": [{"identifiers": [{"type": "NAME", "value": "H2O"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 150.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "Stirring at this temperature"}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "to warm to room temperature", "temperature": {"control": {"type": "AMBIENT"}}}, {"type": "FILTRATION", "details": "the precipitated solid was collected by filtration"}], "outcomes": [{"reaction_time": {"value": 4.0, "units": "DAY"}, "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. ### Procedure: A solution of methyl imidocarbamate sulfate (10 g), 28% sodium methoxide (26 mL) and ethyl 2-[(2′-cyanobiphenyl-4-yl)methyl]-3-oxohexanoate (15.8 g) in methanol (100 mL) was stirred overnight at room temperature. The solvent was evaporated under reduced pressure, and water and acetic acid were added. The precipitated solid was collected by filtration, washed with water and diethyl ether to give the title compound (2.62 g, 16%) as a colorless solid. ### ORD JSON:	{"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl imidocarbamate sulfate"}], "amount": {"mass": {"value": 10.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium methoxide"}], "amount": {"volume": {"value": 26.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethyl 2-[(2\u2032-cyanobiphenyl-4-yl)methyl]-3-oxohexanoate"}], "amount": {"mass": {"value": 15.8, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methanol"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The solvent was evaporated under reduced pressure, and water and acetic acid", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "acetic acid"}], "reaction_role": "WORKUP"}]}}, {"type": "ADDITION", "details": "were added"}, {"type": "FILTRATION", "details": "The precipitated solid was collected by filtration"}, {"type": "WASH", "details": "washed with water and diethyl ether", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "diethyl ether"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 2.62, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 16.0}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 16.1}}], "isolated_color": "colorless", "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. ### Procedure: 1-(4-Methoxy-3-trifluoromethyl-phenyl)-2,5-dimethyl-1H-imidazole-4-carboxylic acid ethyl ester (0.8 g, 2.3 mmol) and 2-chloro-4-methylpyridine (0.36 g, 2.8 mmol) were dissolved in 10 mL toluene. This solution was dropped to a cold (0° C.) mixture of potassium bis(trimethylsilyl)amide (1.17 g, 5.84 mmol) in 15 mL toluene. The reaction mixture was stirred for 90 min. at 0° C. 0.4 mL acetic acid were added, and the mixture extracted with water, saturated NaHCO3-Solution and brine. The aqueous layer was washed with toluene (100 mL). The combined organic extracts were dried with sodium sulfate and filtered. The solvent was evaporated, and the crude product [(0.8 g, 81%), [MS: m/e=424.5 (M+H+)] was used without any further purification for the next step. ### ORD JSON:	{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "acetic acid"}], "amount": {"volume": {"value": 0.4, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "1-(4-Methoxy-3-trifluoromethyl-phenyl)-2,5-dimethyl-1H-imidazole-4-carboxylic acid ethyl ester"}], "amount": {"mass": {"value": 0.8, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-chloro-4-methylpyridine"}], "amount": {"mass": {"value": 0.36, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "toluene"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "potassium bis(trimethylsilyl)amide"}], "amount": {"mass": {"value": 1.17, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "toluene"}], "amount": {"volume": {"value": 15.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 0.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "The reaction mixture was stirred for 90 min. at 0\u00b0 C"}, "conditions_are_dynamic": true}, "workups": [{"type": "EXTRACTION", "details": "the mixture extracted with water, saturated NaHCO3-Solution and brine", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "NaHCO3"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "brine"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "The aqueous layer was washed with toluene (100 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "toluene"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "The combined organic extracts were dried with sodium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CUSTOM", "details": "The solvent was evaporated"}, {"type": "CUSTOM", "details": "the crude product [(0.8 g, 81%), [MS: m/e=424.5 (M+H+)] was used without any further purification for the next step", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "crude product"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 90.0, "units": "MINUTE"}, "products": [{}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To a solution of tert-butyl 4-{[2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-yl](hydroxy)methyl}piperidine-1-carboxylate (200 mg, 0.36 mmol) in dichloromethane (10 mL) was added Dess-Martin reagents (226 mg, 0.54 mmol). The resulting mixture was stirred at room temperature until the reaction was complete monitoring by LC/MS and then concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (eluting with 20-30% ethyl acetate in petroleum ether) to afford 150 mg of the desired product. MS (ESI+) [(M+H)+] 550. ### ORD JSON:	{"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "tert-butyl 4-{[2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-yl](hydroxy)methyl}piperidine-1-carboxylate"}], "amount": {"mass": {"value": 200.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Dess-Martin"}], "amount": {"mass": {"value": 226.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "The resulting mixture was stirred at room temperature until the reaction"}, "conditions_are_dynamic": true}, "workups": [{"type": "CONCENTRATION", "details": "concentrated in vacuo"}, {"type": "CUSTOM", "details": "The residue was purified by flash column chromatography on silica gel (eluting with 20-30% ethyl acetate in petroleum ether)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "petroleum ether"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "desired product"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 150.0, "units": "MILLIGRAM"}}}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: Similar procedure as described in example 10 was used, starting from 3-chloro-phenol and (1-chloro-6-methoxy-isoquinolin-3-yl)-(5-methyl-1H-pyrazol-3-yl)-amine to give [1-(3-Chloro-phenoxy)-6-methoxy-isoquinolin-3-yl]-(5-methyl-1H-pyrazol-3-yl)-amine. LC-MS m/e 382(MH+). ### ORD JSON:	{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "3-chloro-phenol"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "(1-chloro-6-methoxy-isoquinolin-3-yl)-(5-methyl-1H-pyrazol-3-yl)-amine"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "[1-(3-Chloro-phenoxy)-6-methoxy-isoquinolin-3-yl]-(5-methyl-1H-pyrazol-3-yl)-amine"}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A solution of 140 g of ethylenediamine and 300 g of 2,5-dimethoxytetrahydrofuran in 2000 ml of dioxane and 1700 ml of glacial acetic acid is stirred and refluxed for 6 hours. The reaction mixture is then cooled and the solvents evaporated under reduced pressure at 60°. The dark residue is taken up in methylene chloride and ice and basified with 3N aqueous sodium hydroxide. The organic layer is separated and extracted into 5 N aqueous hydrochloric acid. The acid extract is made basic with cooling and is extracted with methylene chloride. The organic phase is dried over magnesium sulfate, treated with 10 g of charcoal and filtered. The methylene chloride is evaporated under reduced pressure to give an N-acetyl-2-(1-pyrrolyl)-ethylamine as an oil. ### ORD JSON:	{"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ethylenediamine"}], "amount": {"mass": {"value": 140.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2,5-dimethoxytetrahydrofuran"}], "amount": {"mass": {"value": 300.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dioxane"}], "amount": {"volume": {"value": 2000.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "acetic acid"}], "amount": {"volume": {"value": 1700.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "refluxed for 6 hours", "duration": {"value": 6.0, "units": "HOUR"}}, {"type": "TEMPERATURE", "details": "The reaction mixture is then cooled"}, {"type": "CUSTOM", "details": "the solvents evaporated under reduced pressure at 60\u00b0"}, {"type": "CUSTOM", "details": "The organic layer is separated"}, {"type": "EXTRACTION", "details": "extracted into 5 N aqueous hydrochloric acid", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "reaction_role": "WORKUP"}]}}, {"type": "EXTRACTION", "details": "The acid extract"}, {"type": "TEMPERATURE", "details": "with cooling"}, {"type": "EXTRACTION", "details": "is extracted with methylene chloride", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "methylene chloride"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "The organic phase is dried over magnesium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "magnesium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "ADDITION", "details": "treated with 10 g of charcoal", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "charcoal"}], "amount": {"mass": {"value": 10.0, "units": "GRAM"}}, "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CUSTOM", "details": "The methylene chloride is evaporated under reduced pressure", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "methylene chloride"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "N-acetyl-2-(1-pyrrolyl)-ethylamine"}], "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. ### Procedure: Using 1.02 g of 2-fluoro-4-bromobenzaldehyde, 0.33 g of malononitrile, 8 ml of ethanol, 1.5 ml of water and 57 mg of sodium borohydride, and according to the process described in the REFERENCE PRODUCTION EXAMPLE 19, there was obtained 1.21 g of (2-fluoro-4-bromobenzyl)malononitrile (the intermediate (29)). ### ORD JSON:	{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium borohydride"}], "amount": {"mass": {"value": 57.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 1.5, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2-fluoro-4-bromobenzaldehyde"}], "amount": {"mass": {"value": 1.02, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "malononitrile"}], "amount": {"mass": {"value": 0.33, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m0_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "intermediate ( 29 )"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"volume": {"value": 8.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "(2-fluoro-4-bromobenzyl)malononitrile"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 1.21, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: Prepared analogously to Example 1g from 3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzoic acid, TBTU, diisopropylethylamine, and N-[1-(5-chlorobenzimidazol-2-yl)ethyl]ethylamine in tetrahydrofuran. Yield: 36%; Rf value: 0.45 (silica gel; dichloromethane/ethanol=9:1); C24H27ClN4O2 (438.96); mass spectrum: (M−H)−=437/439 (chlorine isotope). ### ORD JSON:	{"inputs": {"m1_m2_m3_m4_m7": {"components": [{"identifiers": [{"type": "NAME", "value": "3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzoic acid"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "TBTU"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "diisopropylethylamine"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "N-[1-(5-chlorobenzimidazol-2-yl)ethyl]ethylamine"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tetrahydrofuran"}], "reaction_role": "SOLVENT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "chlorine"}], "reaction_role": "REACTANT"}]}, "m8": {"components": [{"identifiers": [{"type": "NAME", "value": "dichloromethane ethanol"}], "reaction_role": "SOLVENT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "C24H27ClN4O2"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"measurements": [{"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 36.0}}]}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A mixture of 1,5-bis(4-methoxyphenyl)pentane of Example 8 (60 g, 0.21 mole), 150 ml of hydrobromic acid (47%) and 200 ml of glacial acetic acid was refluxed for 4.5 hours. It was concentrated to a thick liquid, dissolved in ethyl acetate, washed with water, dried over anhydrous magnesium sulfate and concentrated to give 53.0 g of a thick oil. NMR and TLC confirmed the structure. ### ORD JSON:	{"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "1,5-bis(4-methoxyphenyl)pentane"}], "amount": {"mass": {"value": 60.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "hydrobromic acid"}], "amount": {"volume": {"value": 150.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "acetic acid"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "was refluxed for 4.5 hours", "duration": {"value": 4.5, "units": "HOUR"}}, {"type": "CONCENTRATION", "details": "It was concentrated to a thick liquid"}, {"type": "DISSOLUTION", "details": "dissolved in ethyl acetate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "washed with water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "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"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "thick oil"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 53.0, "units": "GRAM"}}}], "isolated_color": "thick", "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. ### Procedure: A solution containing 0.87 g of 4-trifluoromethylbenzaldehyde, 6-(4-aminophenyl-4,5-dihydropyridazin-3(2H)one, 1 ml of acetic acid and 10 ml of N,N-dimethylacetamide in 40 ml of ethanol was refluxed for 5 h. The product was filtered and washed with ethanol. Yield 0.7 g (41%), m.p. 245°-247° C. ### ORD JSON:	{"inputs": {"m2_m3_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "4-aminophenyl-4,5-dihydropyridazin-3(2H)one"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "acetic acid"}], "amount": {"volume": {"value": 1.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "N,N-dimethylacetamide"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"volume": {"value": 40.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "4-trifluoromethylbenzaldehyde"}], "amount": {"mass": {"value": 0.87, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "FILTRATION", "details": "The product was filtered"}, {"type": "WASH", "details": "washed with ethanol", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethanol"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To a solution of 7-(pyridin-4-yl)thieno[3,2-d]pyridazin-4(5H)-one (100 mg, 0.44 mmol) from example 2.3, 2-quinolin-2-yl-ethanol from example a1 (83 mg, 0.48 mmol) and PPh3 (343 mg, 1.31 mmol) in DCM (10 mL), DEAD (228 mg, 1.31 mmol) was added dropwise. The mixture stirred at room temperature for 3 h, concentrated and the purified by Prep-HPLC to give the title compound as a white solid (20 mg, 11.8% yield). ### ORD JSON:	{"inputs": {"m1_m2_m3_m5_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "7-(pyridin-4-yl)thieno[3,2-d]pyridazin-4(5H)-one"}], "amount": {"mass": {"value": 100.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-quinolin-2-yl-ethanol"}], "amount": {"mass": {"value": 83.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "PPh3"}], "amount": {"mass": {"value": 343.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DEAD"}], "amount": {"mass": {"value": 228.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DCM"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "The mixture stirred at room temperature for 3 h"}, "conditions_are_dynamic": true}, "workups": [{"type": "CONCENTRATION", "details": "concentrated"}, {"type": "CUSTOM", "details": "the purified by Prep-HPLC"}], "outcomes": [{"reaction_time": {"value": 3.0, "units": "HOUR"}, "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": 11.8}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 11.8}}], "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. ### Procedure: A mixture composed of 4-amino-N-(2-chloroethyl)-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-7,8-dihydro-2H-6-thia-1,2,3,5-tetraazaacenaphthylene-7-carboxamide of Example 16 (20 mg), isobutylamine (0.8 mL) and dioxane (3 mL) was heated under reflux for 16 hours, and then the reaction mixture was concentrated under reduced pressure. The resulting residue was purified by reversed phase liquid chromatography to obtain the title compound (6 mg, 28%) as a solid. ### ORD JSON:	{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "4-amino-N-(2-chloroethyl)-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-7,8-dihydro-2H-6-thia-1,2,3,5-tetraazaacenaphthylene-7-carboxamide"}], "amount": {"mass": {"value": 20.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "isobutylamine"}], "amount": {"volume": {"value": 0.8, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "dioxane"}], "amount": {"volume": {"value": 3.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "was heated"}, {"type": "TEMPERATURE", "details": "under reflux for 16 hours", "duration": {"value": 16.0, "units": "HOUR"}}, {"type": "CONCENTRATION", "details": "the reaction mixture was concentrated under reduced pressure"}, {"type": "CUSTOM", "details": "The resulting residue was purified by reversed phase liquid chromatography"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 6.0, "units": "MILLIGRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 28.0}}], "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. ### Procedure: 700 g of cyclopentene are added dropwise to 610 g of 3,5-dimethylphenol and 60 g of p-toluene sulphonic acid at 120° C. The catalyst is removed by washing with sodium hydrogen carbonate solution. The mixture is fractionated. At boiling point 141° C (0.6 mm Hg) 591 g of 3,5-dimethyl-2,6-dicyclopentylphenol are obtained. Melting point: 69° C. ### ORD JSON:	{"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "cyclopentene"}], "amount": {"mass": {"value": 700.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "3,5-dimethylphenol"}], "amount": {"mass": {"value": 610.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "p-toluene sulphonic acid"}], "amount": {"mass": {"value": 60.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The catalyst is removed"}, {"type": "WASH", "details": "by washing with sodium hydrogen carbonate solution", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium hydrogen carbonate"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "3,5-dimethyl-2,6-dicyclopentylphenol"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 591.0, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 4-Amino-2-bromothiazole hydrobromide (52 g, 0.2 m) was suspended in acetic anhydride (200 ml) then treated dropwise with pyridine (100 ml), maintaining the temperature at 0° C. by means of an ice bath. After the addition was complete, the reaction mixture was stirred for 2 h. at room temperature then poured onto 20% aqueous sodium acetate (2 l). The solution was cooled, filtered and the precipitate washed with water (2×200 ml.). The product was air dried and recrystallised from acetone to give the title compound (35 g, 80%). m.p. 165° C. Found: C, 27.5; H, 2.5; N, 12.7. C5H5BrN2OS requires C, 27.2; H, 2.3; N, 12.7%. ### ORD JSON:	{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "acetic anhydride"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "4-Amino-2-bromothiazole hydrobromide"}], "amount": {"mass": {"value": 52.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "pyridine"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium acetate"}], "amount": {"volume": {"value": 2.0, "units": "LITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 0.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "the reaction mixture was stirred for 2 h. at room temperature"}, "conditions_are_dynamic": true}, "workups": [{"type": "ADDITION", "details": "After the addition"}, {"type": "TEMPERATURE", "details": "The solution was cooled"}, {"type": "FILTRATION", "details": "filtered"}, {"type": "WASH", "details": "the precipitate washed with water (2\u00d7200 ml.)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "dried"}, {"type": "CUSTOM", "details": "recrystallised from acetone", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "acetone"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 2.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 35.0, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 80.0}}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: In a mixture of 50 ml of tetrahydrofuran and 250 ml of N,N-dimethylformamide were dissolved 9.46 g of 1,2-dihydro-2-oxoquinoline-3-carboxylic acid and 5.06 g of N-methylmorpholine, and after cooling to −15° C., 6.83 g of isobutyl chlorocarbonate was added dropwise over 10 minutes. After stirring at −15° C. for 10 minutes, 9.73 g of dihexylamine was added dropwise over 5 minutes. After stirring at −15° C. for 4 hours and then at room temperature overnight, the reaction mixture was concentrated under reduced pressure, and the residue, after addition of ethyl acetate, was washed with water, 1N hydrochloric acid, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure. The residue was recrystallized from hexane to give 13.51 g of N,N-dihexyl-1,2-dihydro-2-oxoquinoline-3-carboxamide. ### ORD JSON:	{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "dihexylamine"}], "amount": {"mass": {"value": 9.73, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m5_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "tetrahydrofuran"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "N,N-dimethylformamide"}], "amount": {"volume": {"value": 250.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "1,2-dihydro-2-oxoquinoline-3-carboxylic acid"}], "amount": {"mass": {"value": 9.46, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "N-methylmorpholine"}], "amount": {"mass": {"value": 5.06, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "isobutyl chlorocarbonate"}], "amount": {"mass": {"value": 6.83, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": -15.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "After stirring at \u221215\u00b0 C. for 10 minutes"}, "conditions_are_dynamic": true}, "workups": [{"type": "STIRRING", "details": "After stirring at \u221215\u00b0 C. for 4 hours", "duration": {"value": 4.0, "units": "HOUR"}, "temperature": {"setpoint": {"value": -15.0, "units": "CELSIUS"}}}, {"type": "CONCENTRATION", "details": "at room temperature overnight, the reaction mixture was concentrated under reduced pressure", "duration": {"value": 8.0, "precision": 8.0, "units": "HOUR"}, "temperature": {"control": {"type": "AMBIENT"}}}, {"type": "ADDITION", "details": "the residue, after addition of ethyl acetate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "was washed with water, 1N hydrochloric acid", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium bicarbonate"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "sodium chloride"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "sodium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "After removal of the drying agent"}, {"type": "FILTRATION", "details": "by filtration"}, {"type": "CONCENTRATION", "details": "the filtrate was concentrated under reduced pressure"}, {"type": "CUSTOM", "details": "The residue was recrystallized from hexane", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "hexane"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 10.0, "units": "MINUTE"}, "products": [{"identifiers": [{"type": "NAME", "value": "N,N-dihexyl-1,2-dihydro-2-oxoquinoline-3-carboxamide"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 13.51, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A 50 ml one neck round bottom flask equipped with a Dean Stark trap, condenser and a nitrogen inlet/outlet was charged with 5.0 g (0.038 moles) DL-2-hydroxycaproic acid, 23.95 g (0.151 moles) decyl alcohol, and 0.019 g sulfuric acid. The reactants were heated to 140° C. for 8 hours and water collected as the reaction proceeded. The acid was neutralized by washing three times with 50 ml saturated sodium bicarbonate solution. Approximately 50 ml ether was needed to break the emulsion. The organic layer was collected and dried over magnesium sulfate. Excess decyl alcohol was removed by high vacuum distillation to yield 4.34 g (49% yield) of clear colorless liquid. According to GC the product is 95.74% pure. ### ORD JSON:	{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "one"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "DL-2-hydroxycaproic acid"}], "amount": {"mass": {"value": 5.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "decyl alcohol"}], "amount": {"mass": {"value": 23.95, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sulfuric acid"}], "amount": {"mass": {"value": 0.019, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}}, "conditions": {"temperature": {"setpoint": {"value": 140.0, "units": "CELSIUS"}}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "water collected as the reaction", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "by washing three times with 50 ml saturated sodium bicarbonate solution", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium bicarbonate"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "The organic layer was collected"}, {"type": "DRY_WITH_MATERIAL", "details": "dried over magnesium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "magnesium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "Excess decyl alcohol was removed by high vacuum distillation", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "decyl alcohol"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "clear colorless liquid"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 4.34, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 49.0}}], "isolated_color": "clear colorless", "texture": {"type": "CUSTOM", "details": "liquid"}, "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To a mixture of methyl 1-(2-chlorobenzyl)-3-formyl-2-propylindole-6-carboxylate (263 mg), 2-methyl-2-butene (220 mg) and sodium dihydrogenohosphate (128 mg) in a mixture of tert-butanol (7 ml) and water (1.3 ml) was added sodium chlorite (219 mg) at 20° C. The reaction mixture was stirred at 40° C. for 2 hours. The reaction mixture was acidified with 1N hydrochloric acid at 0° C. and extracted with chloroform three times. The organic phase was dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:2) to give 1-(2-chlorobenzyl)-6-methoxycarbonyl-2-propylindole-3-carboxylic acid (94 mg) as pale yellow crystals. ### ORD JSON:	{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium chlorite"}], "amount": {"mass": {"value": 219.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl 1-(2-chlorobenzyl)-3-formyl-2-propylindole-6-carboxylate"}], "amount": {"mass": {"value": 263.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-methyl-2-butene"}], "amount": {"mass": {"value": 220.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium"}], "reaction_role": "REACTANT"}]}, "m6_m7": {"components": [{"identifiers": [{"type": "NAME", "value": "tert-butanol"}], "amount": {"volume": {"value": 7.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 1.3, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 40.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "The reaction mixture was stirred at 40\u00b0 C. for 2 hours"}, "conditions_are_dynamic": true}, "workups": [{"type": "EXTRACTION", "details": "extracted with chloroform three times", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "chloroform"}], "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": "CUSTOM", "details": "evaporated in vacuo"}, {"type": "CUSTOM", "details": "The residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:2)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "hexane"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 2.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "1-(2-chlorobenzyl)-6-methoxycarbonyl-2-propylindole-3-carboxylic acid"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 94.0, "units": "MILLIGRAM"}}}], "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. ### Procedure: A solution of methyl N-(tert-butoxycarbonyl)-L-cysteinate (2.6 g, 11.0 mmol) in THF (10 ml) stirred at 0° C. under N2 was treated with slow addition of a 1M solution of LiAlH4 in THF (20 mL, 20 mmol). The reaction mixture was slowly warmed up to room temperature and further stirred for 2 h, cooled to 0° C. and quenched with slow addition of water, then poured on a 15% solution of K2CO3 in water (25 mL), shaken well and extracted with DCM (3×100 mL), the organic layers were combined and dried over MgSO4, filtered and concentrated to afford the title compound as colorless oil, kept under N2 atmosphere all the times and used fresh without further purification. Assumed quantitative yield. MS: m/z=230.1 (MNa+). ### ORD JSON:	{"inputs": {"m2_m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "solution"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "LiAlH4"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "THF"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl N-(tert-butoxycarbonyl)-L-cysteinate"}], "amount": {"mass": {"value": 2.6, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "THF"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "further stirred for 2 h"}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "cooled to 0\u00b0 C.", "temperature": {"setpoint": {"value": 0.0, "units": "CELSIUS"}}}, {"type": "CUSTOM", "details": "quenched with slow addition of water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "ADDITION", "details": "poured on a 15% solution of K2CO3 in water (25 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "solution"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "K2CO3"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 25.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "STIRRING", "details": "shaken well"}, {"type": "EXTRACTION", "details": "extracted with DCM (3\u00d7100 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "DCM"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over MgSO4", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "MgSO4"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CONCENTRATION", "details": "concentrated"}], "outcomes": [{"reaction_time": {"value": 2.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "isolated_color": "colorless", "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. ### Procedure: A solution of 6,7,8,9-tetrahydro-3-methoxy-10-methylpyrido[1,2-a]indol-9-one (2.29 g, 10 mmol) and hydroxylamine hydrochloride (1.39 g, 20 mmol) in dry pyridine (40 mL) was refluxed for 2 hours. The reaction mixture was concentrated to 10% of its original volume and distilled water (80 mL) was added. The organic product was extracted with ether (3×60 mL). The combined organic layers were washed with water (100 mL), 5% hydrochloric acid (50 mL), and 10% sodium bicarbonate (50 mL). The separated organic layer was dried over MgSO4, filtered, and evaporated. The residue was recrystallized from methanol/water to afford 2.4 g (98%) of the title compound as gray microcrystals. ### ORD JSON:	{"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "6,7,8,9-tetrahydro-3-methoxy-10-methylpyrido[1,2-a]indol-9-one"}], "amount": {"mass": {"value": 2.29, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "hydroxylamine hydrochloride"}], "amount": {"mass": {"value": 1.39, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "pyridine"}], "amount": {"volume": {"value": 40.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CONCENTRATION", "details": "The reaction mixture was concentrated to 10% of its original volume"}, {"type": "DISTILLATION", "details": "distilled water (80 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 80.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "ADDITION", "details": "was added"}, {"type": "EXTRACTION", "details": "The organic product was extracted with ether (3\u00d760 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ether"}], "amount": {"volume": {"value": 60.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "The combined organic layers were washed with water (100 mL), 5% hydrochloric acid (50 mL), and 10% sodium bicarbonate (50 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "sodium bicarbonate"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "The separated organic layer was dried over MgSO4", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "MgSO4"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CUSTOM", "details": "evaporated"}, {"type": "CUSTOM", "details": "The residue was recrystallized from methanol/water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "methanol water"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 2.4, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 98.0}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 98.2}}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A solution of tert-butyl (1S,2R)-2-(7-bromo-4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate (10 mg, 0.020 mmol) in HCl-dioxane(999 μL, 4.00 mmol) was stirred at RT for 2 h. The mixture was concentrated to a residue, diluted with Et2O (3 mL), and sonicated to yield a white precipitate, which was filtered and dried overnight in a lyophilizer to give an HCl salt of the title compound as a white solid (1.8 mg, 21%). [M+H] calc'd for C17H21BrN6O, 406. found, 406. ### ORD JSON:	{"inputs": {"m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "tert-butyl (1S,2R)-2-(7-bromo-4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate"}], "amount": {"mass": {"value": 10.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "HCl dioxane"}], "amount": {"volume": {"value": 999.0, "units": "MICROLITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CONCENTRATION", "details": "The mixture was concentrated to a residue"}, {"type": "ADDITION", "details": "diluted with Et2O (3 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Et2O"}], "amount": {"volume": {"value": 3.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "sonicated"}, {"type": "CUSTOM", "details": "to yield a white precipitate, which"}, {"type": "FILTRATION", "details": "was filtered"}, {"type": "CUSTOM", "details": "dried overnight in a lyophilizer", "duration": {"value": 8.0, "precision": 8.0, "units": "HOUR"}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "HCl"}], "reaction_role": "PRODUCT"}, {"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 1.8, "units": "MILLIGRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 21.0}}], "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. ### Procedure: In an inert atmosphere NaH (2.7 g; 112 mmol) was suspended in DMF (80 ml). At 0-5° C. 5-benzyloxy-2-(4-benzyloxyphenyl)-3-methyl-1H-indole (11 g; 26 mmol) was added and the suspension was stirred for 30 minutes. Then a solution of 4-(2-azepan-1-yl-ethoxy)benzyl chloride (8 g; 26 mmol) in DMF (30 ml) was added dropwise within 1 hour. The cooling was shut down and the reaction mixture was stirred for another 2.5 hours. Then, water (1.2 ml) was carefully added dropwise to the reaction mixture and the reaction mixture was filtered through a thin layer of celite. Another 35 ml of water were added dropwise to the brightly yellow filtrate under intensive stirring. ### ORD JSON:	{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 1.2, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "NaH"}], "amount": {"mass": {"value": 2.7, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "5-benzyloxy-2-(4-benzyloxyphenyl)-3-methyl-1H-indole"}], "amount": {"mass": {"value": 11.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m3_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(2-azepan-1-yl-ethoxy)benzyl chloride"}], "amount": {"mass": {"value": 8.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DMF"}], "amount": {"volume": {"value": 30.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "DMF"}], "amount": {"volume": {"value": 80.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "the suspension was stirred for 30 minutes"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "At 0-5\u00b0 C", "temperature": {"setpoint": {"value": 2.5, "precision": 2.5, "units": "CELSIUS"}}}, {"type": "STIRRING", "details": "the reaction mixture was stirred for another 2.5 hours", "duration": {"value": 2.5, "units": "HOUR"}}, {"type": "FILTRATION", "details": "the reaction mixture was filtered through a thin layer of celite"}, {"type": "ADDITION", "details": "Another 35 ml of water were added dropwise to the brightly yellow filtrate under intensive stirring", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 35.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}], "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. ### Procedure: A solution of EXAMPLE 56D (4.5 g, 10 mmol) in acetic acid (100 mL) was treated with cyclohexanone (2 mL, 20 mmol) at ambient temperature for 4 days. The mixture was concentrated and the residue partitioned between dilute sodium hydroxide and ethyl acetate. The organic layer was washed with water and concentrated and the residue purified by flash chromatography on silica gel using ethyl acetate to give 3.8 g (71%) of the title compound. MS (DCI): m/z 537 (M+H)+. ### ORD JSON:	{"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "solution"}], "amount": {"mass": {"value": 4.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "cyclohexanone"}], "amount": {"volume": {"value": 2.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "acetic acid"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CONCENTRATION", "details": "The mixture was concentrated"}, {"type": "CUSTOM", "details": "the residue partitioned between dilute sodium hydroxide and ethyl acetate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium hydroxide"}], "reaction_role": "WORKUP"}, {"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": "CONCENTRATION", "details": "concentrated"}, {"type": "CUSTOM", "details": "the residue purified by flash chromatography on silica gel"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 3.8, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 71.0}}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: LiOH (3.0 eq.) was added to a 0.05 M solution of methyl (9R,11S,14S)-14-tert-butyl-13-oxo-8-oxa-12,15-diazatetracyclo[20.3.1.12,6.1 9,12]octacosa-1(26),2(28),3,5,22,24-hexaene-11-carboxylate 104 in a mixture of THF:EtOH:H2O (2:1:1). The reaction mixture was stirred at 40° C. for 2 h then the solvent was evaporated under reduced pressure. Aqueous HCl (1N) was added to reach pH=6 and the mixture was evaporated to dryness to yield a dark solid which was used without further purification. MS (ES+) m/z 493 (M+H)+. ### ORD JSON:	{"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "LiOH"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "solution"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methyl (9R,11S,14S)-14-tert-butyl-13-oxo-8-oxa-12,15-diazatetracyclo[20.3.1.12,6.1 9,12]octacosa-1(26),2(28),3,5,22,24-hexaene-11-carboxylate"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "THF EtOH H2O"}], "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 40.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "The reaction mixture was stirred at 40\u00b0 C. for 2 h"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "the solvent was evaporated under reduced pressure"}, {"type": "ADDITION", "details": "Aqueous HCl (1N) was added", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "HCl"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "the mixture was evaporated to dryness"}, {"type": "CUSTOM", "details": "to yield a dark solid which"}, {"type": "CUSTOM", "details": "was used without further purification"}], "outcomes": [{"reaction_time": {"value": 2.0, "units": "HOUR"}, "products": [{}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: contacting benzene and hydrogen with a catalyst under hydroalkylation conditions to produce cyclohexylbenzene; ### ORD JSON:	{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrogen"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "benzene"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "cyclohexylbenzene"}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: Fluvastatin methyl ester (10.0 g) was dissolved in acetone (150 ml) and a solution of NaOH (0.94 g) in MeOH (10 ml) was added. After 26.5 h, NaOH (0.47 g) was added and the mixture was stirred at room temperature over night. The product was isolated by filtration under nitrogen, washed with acetone (20 ml) and dried at 50EC in a vacuum oven for 23 h to obtain 8.01 g of fluvastatin sodium crystal Form LXVII. ### ORD JSON:	{"inputs": {"m1_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Fluvastatin methyl ester"}], "amount": {"mass": {"value": 10.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "acetone"}], "amount": {"volume": {"value": 150.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "NaOH"}], "amount": {"mass": {"value": 0.94, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "MeOH"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "NaOH"}], "amount": {"mass": {"value": 0.47, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "the mixture was stirred at room temperature over night"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The product was isolated by filtration under nitrogen"}, {"type": "WASH", "details": "washed with acetone (20 ml)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "acetone"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "dried at 50EC in a vacuum oven for 23 h", "duration": {"value": 23.0, "units": "HOUR"}}], "outcomes": [{"reaction_time": {"value": 26.5, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "fluvastatin sodium"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 8.01, "units": "GRAM"}}}], "texture": {"type": "CRYSTAL", "details": "crystal"}, "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To a solution of (2-ethoxy-4′-fluoro-biphenyl-4-yl)-methanol (0.42 g, 1.71 mmol, 1.0 equiv) in dichloromethane (20 mL) was added activated MnO2 (2.97 g, 34.11 mmol, 20.0 equiv). The reaction mixture was stirred vigorously for 3 h at ambient temperature and then filtered through Hyflo Super Cel. The organic phase was concentrated by evaporation under reduced pressure and the crude reaction product purified with column chromatography on silica eluting with hexane/ethyl acetate (4:1) providing 0.33 g (79%) of the title compound. MS (EI): 244.1 [M]+. ### ORD JSON:	{"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "(2-ethoxy-4\u2032-fluoro-biphenyl-4-yl)-methanol"}], "amount": {"mass": {"value": 0.42, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "MnO2"}], "amount": {"mass": {"value": 2.97, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "The reaction mixture was stirred vigorously for 3 h at ambient temperature"}, "conditions_are_dynamic": true}, "workups": [{"type": "FILTRATION", "details": "filtered through Hyflo Super Cel"}, {"type": "CONCENTRATION", "details": "The organic phase was concentrated by evaporation under reduced pressure"}, {"type": "CUSTOM", "details": "the crude reaction product"}, {"type": "CUSTOM", "details": "purified with column chromatography on silica eluting with hexane/ethyl acetate (4:1)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "hexane ethyl acetate"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 3.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.33, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 79.0}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 79.0}}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To a stirred solution of 2-chloro-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-(isopropylamino)isonicotinamide (0.58 g, 1.67 mmol), boronic acid (0.277 g, 1.84 mmol) in dioxane/water mixture (7 mL+3 mL), Na2CO3 (0.64 g, 6.037 mmol) was added and reaction mass purged for 15 min with argon. Then Pd(PPh3)4 (0.194 g, 0.168 mmol) was added and argon was purged again for 10 min. Reaction mass was heated at 100° C. for 3 h. On completion, reaction mass filtered through celite and celite bed washed with ethyl acetate. Combined filtrates were dried over Na2SO4 and solvent removed under reduced pressure to afford crude material which was purified by column over silica gel to obtain N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-(4-formylphenyl)-6-(isopropylamino)isonicotinamide (0.6 g, 85.7%). ### ORD JSON:	{"inputs": {"m1_m2_m4_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "2-chloro-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-(isopropylamino)isonicotinamide"}], "amount": {"mass": {"value": 0.58, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "boronic acid"}], "amount": {"mass": {"value": 0.277, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Na2CO3"}], "amount": {"mass": {"value": 0.64, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dioxane water"}], "amount": {"volume": {"value": 7.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "Pd(PPh3)4"}], "amount": {"mass": {"value": 0.194, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}}, "conditions": {"temperature": {"setpoint": {"value": 100.0, "units": "CELSIUS"}}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "reaction mass"}, {"type": "CUSTOM", "details": "purged for 15 min with argon", "duration": {"value": 15.0, "units": "MINUTE"}}, {"type": "CUSTOM", "details": "argon was purged again for 10 min", "duration": {"value": 10.0, "units": "MINUTE"}}, {"type": "CUSTOM", "details": "Reaction mass"}, {"type": "CUSTOM", "details": "On completion, reaction mass"}, {"type": "FILTRATION", "details": "filtered through celite and celite bed"}, {"type": "WASH", "details": "washed with ethyl acetate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "Combined filtrates were dried over Na2SO4 and solvent", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Na2SO4"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "removed under reduced pressure"}, {"type": "CUSTOM", "details": "to afford crude material which"}, {"type": "CUSTOM", "details": "was purified by column over silica gel"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-(4-formylphenyl)-6-(isopropylamino)isonicotinamide"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.6, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 85.7}}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: EDC (128 mg, 0.668 mmol) was added to a stirring solution of the crude 2-(4-fluorophenyl)-4-nitro-5-(3-(2-phenylpropan-2-ylcarbamoyl)phenyl)benzofuran-3-carboxylic acid (300 mg, 0.557 mmol), methanamine (306 μL, 0.613 mmol), 1-hydroxy-7-azabenzotriazole (83 mg, 0.613 mmol), DIEA (204 μL, 1.170 mmol) in DCM (5.5 mL) at rt. It was allowed to stir for 3 days. The slurry had gone into solution over that period of time. The mixture was concentrated and purified on silica gel (BIOTAGE®, EtOAc/hexanes gradient, fraction collection at λ=254 nm) to give the titled compound (220 mg, 95%). 1H NMR (500 MHz, CD3OD) δ ppm 7.90-7.99 (3H, m), 7.85-7.90 (1H, m), 7.82-7.84 (1H, m), 7.49-7.56 (3H, m), 7.45 (2H, d, J=7.32 Hz), 7.27-7.34 (4H, m), 7.19 (1H, t, J=7.32 Hz), 2.87 (3H, s), 1.76 (6H, s). LC-MS retention time: 1.62 min; m/z (MH+): 552. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters XBridge 5u C18 4.6×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 5 ml/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 2 min, a hold time of 1 min, and an analysis time of 3 min where solvent A was 5% acetonitrile/95% H2O/10 mM ammonium acetate and solvent B was 5% H2O/95% acetonitrile/10 mM ammonium acetate. MS data was determined using a MICROMASS® Platform for LC in electrospray mode. Additional HPLC method: Solvent A=5% CH3CN/95% H2O/0.1% TFA, Solvent B=95% CH3CN/5% H2O/0.1% TFA, Start % B=10, Final % B=100, Gradient time=15 min, Stop time=18 min, Flow Rate=1 ml/min. Column: Waters Sunfire C-18, 4.6×150 mm, 3.5 μm, Rt=13.60 min, purity=94%; Column: Waters XBridge phenyl column 4.6×150 mm, 3.5 μm, Rt=12.66 min, purity=96%. ### ORD JSON:	{"inputs": {"m1_m2_m3_m4_m5_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "EDC"}], "amount": {"mass": {"value": 128.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-(4-fluorophenyl)-4-nitro-5-(3-(2-phenylpropan-2-ylcarbamoyl)phenyl)benzofuran-3-carboxylic acid"}], "amount": {"mass": {"value": 300.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methanamine"}], "amount": {"volume": {"value": 306.0, "units": "MICROLITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1-hydroxy-7-azabenzotriazole"}], "amount": {"mass": {"value": 83.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DIEA"}], "amount": {"volume": {"value": 204.0, "units": "MICROLITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DCM"}], "amount": {"volume": {"value": 5.5, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "to stir for 3 days"}, "conditions_are_dynamic": true}, "workups": [{"type": "WAIT", "details": "The slurry had gone into solution over that period of time"}, {"type": "CONCENTRATION", "details": "The mixture was concentrated"}, {"type": "CUSTOM", "details": "purified on silica gel (BIOTAGE\u00ae, EtOAc/hexanes gradient, fraction collection at \u03bb=254 nm)"}], "outcomes": [{"reaction_time": {"value": 3.0, "units": "DAY"}, "products": [{"identifiers": [{"type": "NAME", "value": "titled compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 220.0, "units": "MILLIGRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 95.0}}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A mixture of 820 mg (3.3 mmol) of 1,4-dibutyl-2-methyl-1,4,2-diazaphospholidine-3,5-dione (cf. Ex. 3) with 6.27 g (44 mmol) of methyl iodide (from Aldrich) was heated at reflux (bath temperature: to 80° C.) while stirring with a magnetic stirrer bar for 24 h. The yellow mixture, whose viscosity had risen noticeably, was analysed by NMR spectroscopy without further workup: ### ORD JSON:	{"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "1,4-dibutyl-2-methyl-1,4,2-diazaphospholidine-3,5-dione"}], "amount": {"mass": {"value": 820.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methyl iodide"}], "amount": {"mass": {"value": 6.27, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 80.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "while stirring with a magnetic stirrer bar for 24 h"}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "was heated"}], "outcomes": [{"reaction_time": {"value": 24.0, "units": "HOUR"}, "products": [{}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: (Griffiths, P. G. et al Synthesis of the radical scavenger 1,1,3,3-tetramethylisoindolin-2-yloxyl. Aust. J. Chem. 1983, 36, 397-401; Chan, K. S. et al. Reactions of nitroxides with metalloporphyrin alkyls bearing beta hydrogens: aliphatic carbon-carbon bond activation by metal centered radicals. J. Organomet. Chem. 2008, 693, 399-407). The protected benzyl-amine 16 (1.864 g, 7.02 mmol) was dissolved in AcOH (34 mL) in a Parr flask, and 10% Pd/C (169.5 mg) was added. (The reaction was splited in 3 batches.) The flask was placed in a high pressure reactor. The reactor was charged with H2 and purged for 5 cycles and was finally pressurized with H2 at 4 bars (60 psi). After stirring at rt for 3 h, the reaction mixture was filtered through Celite, and the solvent removed in vacuo. The resulting residue was dissolved in water (5 mL) and the solution neutralized with 2.5N NaOH (pH 11.5), and extracted with Et2O (3×50 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo to yield 1.165 g (95%) of the crude title compound as slightly yellow crystals. mp 36.0-36.5° C. 1H NMR (300 MHz, CDCl3) δ 7.30-7.23 (m, 2 H), 7.18-7.11 (m, 2 H), 1.86 (bs, 1 H), 1.48 (s, 12 H). ### ORD JSON:	{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrogens"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "metalloporphyrin"}], "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "1,1,3,3-tetramethylisoindolin-2-yloxyl"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "nitroxides"}], "reaction_role": "REACTANT"}]}, "m5_m6_m7": {"components": [{"identifiers": [{"type": "NAME", "value": "benzyl-amine"}], "amount": {"mass": {"value": 1.864, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "AcOH"}], "amount": {"volume": {"value": 34.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "Pd/C"}], "amount": {"mass": {"value": 169.5, "units": "MILLIGRAM"}}, "reaction_role": "CATALYST"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "After stirring at rt for 3 h"}, "conditions_are_dynamic": true}, "workups": [{"type": "ADDITION", "details": "was added"}, {"type": "CUSTOM", "details": "(The reaction was splited in 3 batches"}, {"type": "CUSTOM", "details": ") The flask was placed in a high pressure reactor"}, {"type": "ADDITION", "details": "The reactor was charged with H2"}, {"type": "CUSTOM", "details": "purged for 5 cycles"}, {"type": "FILTRATION", "details": "the reaction mixture was filtered through Celite"}, {"type": "CUSTOM", "details": "the solvent removed in vacuo"}, {"type": "DISSOLUTION", "details": "The resulting residue was dissolved in water (5 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "EXTRACTION", "details": "extracted with Et2O (3\u00d750 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Et2O"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "The combined organic layers were dried (Na2SO4)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Na2SO4"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CONCENTRATION", "details": "concentrated in vacuo"}], "outcomes": [{"reaction_time": {"value": 3.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "crude title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 1.165, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 95.0}}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: N-(1-Acetyl-5-chloromethyl-4,6-dimethylindolin-7-yl)-2,2-dimethyl-propanamide (2.0 g) was dissolved in CHCl3 (40 ml) and (CH3)2NH. HCl (3.5 g) and K2CO3 (11.8 g) were added, which was followed by stirring at room temperature for 4 hr. CHCl3 (300 ml) was added, and the mixture was washed successively with 2N-hydrochloric acid, 2N aqueous NaOH and saturated brine, and dried over anhydrous sodium sulfate. CHCl3 was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: CHCl3/MeOH=10/1−1/1) to give 700 mg of N-(1-acetyl-5-dimethylaminomethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide. ### ORD JSON:	{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "(CH3)2NH"}], "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "CHCl3"}], "amount": {"volume": {"value": 300.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "HCl"}], "amount": {"mass": {"value": 3.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "K2CO3"}], "amount": {"mass": {"value": 11.8, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m1_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "N-(1-Acetyl-5-chloromethyl-4,6-dimethylindolin-7-yl)-2,2-dimethyl-propanamide"}], "amount": {"mass": {"value": 2.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "CHCl3"}], "amount": {"volume": {"value": 40.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "by stirring at room temperature for 4 hr"}, "conditions_are_dynamic": true}, "workups": [{"type": "WASH", "details": "the mixture was washed successively with 2N-hydrochloric acid, 2N aqueous NaOH and saturated brine", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "NaOH"}], "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": "CUSTOM", "details": "CHCl3 was evaporated under reduced pressure", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "CHCl3"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "The residue was purified by silica gel column chromatography (eluent: CHCl3/MeOH=10/1\u22121/1)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "CHCl3 MeOH"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 4.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "N-(1-acetyl-5-dimethylaminomethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 700.0, "units": "MILLIGRAM"}}}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: The Grignard reagent, prepared from 3.68 mmol of 1-bromo-4-(1,1-dimethoxyethyl)benzene [53578-00-0] and 14.72 mmol of magnesium in 5.5 ml of tetrahydrofuran is added slowly dropwise to a solution of 1.84 mmol of 6,7-dihydro-5H-imidazo[1,5-a]pyridin-8-one [426219-51-4] in 10 ml of tetrahydrofuran under argon. The reaction mixture is stirred at room temperature for 12 hours and then quenched with 0.5N HCl. It is extracted with dichloromethane and the phases are separated. The aqueous phase is rendered basic with sodium hydrogen carbonate and the precipitated solid is isolated by filtration and dried at 40° C. The title compound is obtained as a greyish solid. Rt=3.42 (Gradient I). By the process described in Example 3 the following compounds are prepared analogously: ### ORD JSON:	{"inputs": {"m1_m2_m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "Grignard reagent"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1-bromo-4-(1,1-dimethoxyethyl)benzene"}], "amount": {"moles": {"value": 3.68, "units": "MILLIMOLE"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "magnesium"}], "amount": {"moles": {"value": 14.72, "units": "MILLIMOLE"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tetrahydrofuran"}], "amount": {"volume": {"value": 5.5, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m4_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "6,7-dihydro-5H-imidazo[1,5-a]pyridin-8-one"}], "amount": {"moles": {"value": 1.84, "units": "MILLIMOLE"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tetrahydrofuran"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "The reaction mixture is stirred at room temperature for 12 hours"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "quenched with 0.5N HCl", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "HCl"}], "reaction_role": "WORKUP"}]}}, {"type": "EXTRACTION", "details": "It is extracted with dichloromethane", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "the phases are separated"}, {"type": "CUSTOM", "details": "the precipitated solid is isolated by filtration"}, {"type": "CUSTOM", "details": "dried at 40\u00b0 C", "temperature": {"setpoint": {"value": 40.0, "units": "CELSIUS"}}}], "outcomes": [{"reaction_time": {"value": 12.0, "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. ### Procedure: (2R,3S)-2-(2-Fluorophenyl)-3-methyl-2-(1H-1,2,4-triazol-1-yl)methyloxirane was reacted with 1-[4-(1H-1,2,3-triazol-1-yl)phenyl]-2(1H,3H)-imidazolone in the same manner as in Working Example 11 to give 1-[(1R,2R)-2-(2-fluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-[4-(1H-1,2,3-triazol-1-yl)phenyl]-2(1H,3H)-imidazolone (Compound 32). ### ORD JSON:	{"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "(2R,3S)-2-(2-Fluorophenyl)-3-methyl-2-(1H-1,2,4-triazol-1-yl)methyloxirane"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1-[4-(1H-1,2,3-triazol-1-yl)phenyl]-2(1H,3H)-imidazolone"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "Compound 32"}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To a solution of 0.5 g (2.4 mmol) 7-methoxy-1-methylquinox-aline-2,3(1H,4H)-dione in 20 ml concentrated sulfuric acid was added at 0° C. 0.25 g (2.48 mmol) potassium nitrate. Stirring was continued at 0° C. for 30 min, and then at 25° C. for 90 min. The reaction mixture was poured into 100 ml icewater to give 0.51 g (84%) of 7-methoxy-1-methyl-6-nitroquinoxaline- 2,3(1H,4H)-dione as a precipitate. M.p. 343° C. NMR (DMSO-d6): 11.9 (1H, broad s), 7.67 (1H, s), 7.0 (1H, s), 3.97 (3H, s), 3.53 (3H, s). ### ORD JSON:	{"inputs": {"m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "7-methoxy-1-methylquinox-aline-2,3(1H,4H)-dione"}], "amount": {"mass": {"value": 0.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sulfuric acid"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "potassium nitrate"}], "amount": {"mass": {"value": 0.25, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "Stirring"}, "conditions_are_dynamic": true}, "workups": [{"type": "WAIT", "details": "at 25\u00b0 C. for 90 min", "duration": {"value": 90.0, "units": "MINUTE"}, "temperature": {"setpoint": {"value": 25.0, "units": "CELSIUS"}}}, {"type": "ADDITION", "details": "The reaction mixture was poured into 100 ml icewater"}], "outcomes": [{"reaction_time": {"value": 30.0, "units": "MINUTE"}, "products": [{"identifiers": [{"type": "NAME", "value": "7-methoxy-1-methyl-6-nitroquinoxaline- 2,3(1H,4H)-dione"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.51, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 84.0}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 84.6}}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A solution of 2-(4-((4-isopropylpiperazin-1-yl)methyl)phenyl)-5,7-dimethoxyquinazolin-4(3H)-one (0.470 g, 0.98 mmol) in 2N HCl (20 mL) was refluxed for 3 days. The resulting mixture was basified with 2N NaOH and extracted with CH2Cl2. The organics were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 30% to 100% of 92:7:1 CHCl3/MeOH/concentrated NH4OH in CH2Cl2, afforded the title compound (0.090 g, 21%) as a light yellow solid. 1H NMR (300 MHz, DMSO-d6): δ 8.12 (d, J=8.3 Hz, 2H), 7.42 (d, J=8.3 Hz, 2H), 6.73 (d, J=2.3 Hz, 1H), 6.53 (d, J=2.3 Hz, 1H), 3.89 (s, 3H), 3.85 (s, 3H), 3.50 (s, 2H), 2.86-2.92 (m, 1H), 2.73-2.77 (m, 2H), 1.85-2.01 (m, 2H), 1.72-1.77 (m, 2H), 1.09-1.38 (m, 4H), 0.94 (d, J=6.2 Hz, 6H). ESI/APCI MS m/z 437 [M+H]+. ### ORD JSON:	{"inputs": {"m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "2-(4-((4-isopropylpiperazin-1-yl)methyl)phenyl)-5,7-dimethoxyquinazolin-4(3H)-one"}], "amount": {"mass": {"value": 0.47, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "HCl"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "NaOH"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "EXTRACTION", "details": "extracted with CH2Cl2", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "CH2Cl2"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "The organics were washed with brine", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "brine"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over anhydrous Na2SO4", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Na2SO4"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CONCENTRATION", "details": "concentrated in vacuo"}, {"type": "CUSTOM", "details": "Purification by flash chromatography on silica gel"}, {"type": "WASH", "details": "eluting with 30% to 100% of 92:7:1 CHCl3/MeOH/concentrated NH4OH in CH2Cl2", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "CHCl3 MeOH"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "NH4OH"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "CH2Cl2"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.09, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 21.0}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 42.1}}], "isolated_color": "light yellow", "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. ### Procedure: To a solution of 7-bromo-6-(4-methoxybenzyl)-3-methyl-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one (100 mg, 0.3 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (92 mg, 0.44 mmol) and sat. sodium carbonate (100 mg, 0.9 mmol) in toluene (20 mL, 0.2 mol) was added tetrakis(triphenylphosphine)palladium(0) (20 mg, 0.01 mmol) under N2 at room temperature. The mixture was heated to reflux overnight. The mixture was stripped down and purified by preparative LC-MS to yield the desired product (50 mg, 37%). LCMS calculated for C24H29N8O2(M+H): 461.2; found 461.2. ### ORD JSON:	{"inputs": {"m1_m2_m3_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "7-bromo-6-(4-methoxybenzyl)-3-methyl-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one"}], "amount": {"mass": {"value": 100.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole"}], "amount": {"mass": {"value": 92.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium carbonate"}], "amount": {"mass": {"value": 100.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "toluene"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tetrakis(triphenylphosphine)palladium(0)"}], "amount": {"mass": {"value": 20.0, "units": "MILLIGRAM"}}, "reaction_role": "CATALYST"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "The mixture was heated"}, {"type": "TEMPERATURE", "details": "to reflux overnight", "duration": {"value": 8.0, "precision": 8.0, "units": "HOUR"}}, {"type": "CUSTOM", "details": "purified by preparative LC-MS"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "desired product"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 50.0, "units": "MILLIGRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 37.0}}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 4-Chloro-3-cyanonitrobenzene (12.5 g, 6.84 mmol) was added portionwise to a stirred N,N-dimethylformamide (50 mL) solution of thiophenol potassium salt [prepared by adding thiophenol (7.1 mL, 6.9 mmol) to a solution of potassium hydroxide (3.84 g, 6.84 mmol) in methanol followed by removal of the methanol in vacuo]. After stirring at 105° C. for 2.5 hours the mixture was poured into ice-water, filtered, the collected solid washed with water, dissolved in 300 mL of refluxing ethanol (charcoal), filtered, treated with 35 mL of water and refrigerated. The resulting pale yellow solid weighed 13.3 g (76%), mp 82°-84° C. 1H--NMR (250 MHz, CDCl3): 6.93 (d, 1H, J=9.0 Hz, aromatic), 7.51-7.62 (m, 5H, aromatic), 8.12(dd, 1H, J=9.2, 2.5 Hz, aromatic), 8.46 (d, 1H, J=2.5 Hz, aromatic). MS (CI, CH4): 257(M+1). ### ORD JSON:	{"inputs": {"m1_m6_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-Chloro-3-cyanonitrobenzene"}], "amount": {"mass": {"value": 12.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "thiophenol potassium salt"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "N,N-dimethylformamide"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "thiophenol"}], "amount": {"volume": {"value": 7.1, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "potassium hydroxide"}], "amount": {"mass": {"value": 3.84, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methanol"}], "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 105.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "After stirring at 105\u00b0 C. for 2.5 hours the mixture"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "prepared"}, {"type": "CUSTOM", "details": "followed by removal of the methanol in vacuo]", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "methanol"}], "reaction_role": "WORKUP"}]}}, {"type": "ADDITION", "details": "was poured into ice-water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ice water"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "WASH", "details": "the collected solid washed with water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "DISSOLUTION", "details": "dissolved in 300 mL of refluxing ethanol (charcoal)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"volume": {"value": 300.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "ADDITION", "details": "treated with 35 mL of water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 35.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 2.5, "units": "HOUR"}, "products": [{}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: ninhydrin, 4-(2-chloro-6-methylphenyl)-semicarbazide hydrochloride ### ORD JSON:	{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "ninhydrin"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(2-chloro-6-methylphenyl)-semicarbazide hydrochloride"}], "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. ### Procedure: Iodomethane (0.2 ml) was added to a stirred suspension of the product from step (i) (0.65 g) and sodium bicarbonate (0.4 g) in ethanol (15 ml) and water (4 ml). After stirring for 30 min, the reaction mixture was washed with water, 1M hydrochloric acid, aqueous sodium bicarbonate, water, dried (MgSO4) and evaporated under reduced pressure. The residue was triturated with ether and filtered. Yield 0.49 g. ### ORD JSON:	{"inputs": {"m1_m2_m3_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "Iodomethane"}], "amount": {"volume": {"value": 0.2, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "product"}], "amount": {"mass": {"value": 0.65, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium bicarbonate"}], "amount": {"mass": {"value": 0.4, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"volume": {"value": 15.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 4.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "After stirring for 30 min"}, "conditions_are_dynamic": true}, "workups": [{"type": "WASH", "details": "the reaction mixture was washed with water, 1M hydrochloric acid, aqueous sodium bicarbonate, water", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "sodium bicarbonate"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried (MgSO4)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "MgSO4"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "evaporated under reduced pressure"}, {"type": "CUSTOM", "details": "The residue was triturated with ether", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ether"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}], "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. ### Procedure: A mixture of 2-bromo-1,5-dimethyl-3-nitrobenzene (1.8 g, 7.8 mmol), Fe powder (2.2 g), concentrated hydrochloric acid (0.3 mL), and EtOH (20 mL) was stirred at 80° C. overnight. Ethyl acetate (20 mL) was subsequently added. The resulting suspension was filtered and the filtrate concentrated. The residue was treated with H2O (10 mL), extracted with ethyl acetate (2×20 mL), washed with brine, dried over anhydrous Na2SO4, and concentrated to give the title compound as a solid (1.2 g, 77%). ### ORD JSON:	{"inputs": {"m1_m4_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "2-bromo-1,5-dimethyl-3-nitrobenzene"}], "amount": {"mass": {"value": 1.8, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "amount": {"volume": {"value": 0.3, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "EtOH"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Fe"}], "amount": {"mass": {"value": 2.2, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "Ethyl acetate"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 80.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "was stirred at 80\u00b0 C. overnight"}, "conditions_are_dynamic": true}, "workups": [{"type": "FILTRATION", "details": "The resulting suspension was filtered"}, {"type": "CONCENTRATION", "details": "the filtrate concentrated"}, {"type": "ADDITION", "details": "The residue was treated with H2O (10 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "H2O"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "EXTRACTION", "details": "extracted with ethyl acetate (2\u00d720 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "washed with brine", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "brine"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over anhydrous Na2SO4", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "Na2SO4"}], "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "concentrated"}], "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": 1.2, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 77.0}}], "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. ### Procedure: 1-(2-Chloropyridin-4-yl)ethan-1-one (110 g, 707 mmol, 1.00 equiv) and methanol (1500 mL) were added to a 3000-mL 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen. NaBH4 (26.4 g, 698 mmol, 1.00 equiv) was added in portions at 0° C. The reaction mixture was stirred overnight at room temperature. The reaction was then quenched by the addition of water (1000 mL). The resulting mixture was concentrated under vacuum and extracted with dichloromethane (3×2000 mL). The combined organic layer was washed with brine (2×2000 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by column chromatography on silica gel (1:5 ethyl acetate/petroleum ether) to afford 1-(2-chloropyridin-4-yl)ethan-1-ol as colorless oil. ### ORD JSON:	{"inputs": {"m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "1-(2-Chloropyridin-4-yl)ethan-1-one"}], "amount": {"mass": {"value": 110.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methanol"}], "amount": {"volume": {"value": 1500.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "NaBH4"}], "amount": {"mass": {"value": 26.4, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "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": "purged"}, {"type": "TEMPERATURE", "details": "maintained with an inert atmosphere of nitrogen"}, {"type": "CUSTOM", "details": "The reaction was then quenched by the addition of water (1000 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 1000.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "CONCENTRATION", "details": "The resulting mixture was concentrated under vacuum"}, {"type": "EXTRACTION", "details": "extracted with dichloromethane (3\u00d72000 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 2000.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "The combined organic layer was washed with brine (2\u00d72000 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "brine"}], "amount": {"volume": {"value": 2000.0, "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 under vacuum"}, {"type": "CUSTOM", "details": "The residue was purified by column chromatography on silica gel (1:5 ethyl acetate/petroleum ether)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate petroleum ether"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 8.0, "precision": 8.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "1-(2-chloropyridin-4-yl)ethan-1-ol"}], "isolated_color": "colorless", "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. ### Procedure: A mixture of 1-(3-chlorobenzyl)-5-(2-chloroethoxymethy)-3-(1-naphthylsulfony)-1H-indazole (0.08 g, 0.16 mmoles) and dimethylamine (0.28 ml, 0.56 mmoles) in DMSO (1 mL) was stirred under nitrogen at 100° C. for 4 hours. Mixture was cooled to room temperature, diluted with water, extracted with EtOAc, washed with water (2×), brine (1×), dried over Na2SO4, and concentrated under vacuum. Compound was purified by flash chromatography using as eluent 5% CH3OH/EtOAc to afford the title compound (0.08 g, 0.15 mmoles). ### ORD JSON:	{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "SOLVENT"}]}, "m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "1-(3-chlorobenzyl)-5-(2-chloroethoxymethy)-3-(1-naphthylsulfony)-1H-indazole"}], "amount": {"mass": {"value": 0.08, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dimethylamine"}], "amount": {"volume": {"value": 0.28, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DMSO"}], "amount": {"volume": {"value": 1.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 100.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "was stirred under nitrogen at 100\u00b0 C. for 4 hours"}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "Mixture was cooled to room temperature", "temperature": {"control": {"type": "AMBIENT"}}}, {"type": "EXTRACTION", "details": "extracted with EtOAc", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "EtOAc"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "washed with water (2\u00d7), brine (1\u00d7)", "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 under vacuum"}, {"type": "CUSTOM", "details": "Compound was purified by flash chromatography"}], "outcomes": [{"reaction_time": {"value": 4.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "AMOUNT", "amount": {"moles": {"value": 0.15, "units": "MILLIMOLE"}}}, {"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.08, "units": "GRAM"}}}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To a stirred solution of 2-methoxy-4-(2-oxoethyl)benzonitrile (1.5 g, 8.5 mmol) in dichloromethane (30 mL) at 0° C. was added 2.8 mL (8.5 mmol) of a 3.0 M solution of methylmagnesium bromide in THF. The reaction mixture was allowed to warm up to rt and stirred for 12 h. The reaction was then quenched by the addition of 10 mL of 1 N hydrochloric acid and extracted with dichloromethane (2×30 mL). The combined organic extracts were dried with magnesium sulfate, filtered, and concentrated in vacuo. The crude residue was purified on silica (30% EtOAc/hexanes as eluent) to afford 4-(2-hydroxypropyl)-2-methoxybenzonitrile. 1H NMR (500 MHz, CDCl3) δ 7.47 (d, 1H, J=7.8 Hz), 6.85 (dd, 1H, J=3.4 Hz), 6.82 (s, 1H), 4.05 (m, 1H), 3.93 (d, 2H), 3.91 (s, 3H), 1.25 (d, 2H, J=6.1 Hz); LCMS: [(M+1)]+=192.30; tR=2.39 min. ### ORD JSON:	{"inputs": {"m1_m4_m2_m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "2-methoxy-4-(2-oxoethyl)benzonitrile"}], "amount": {"mass": {"value": 1.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "solution"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methylmagnesium bromide"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 30.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "THF"}], "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "stirring": {"type": "CUSTOM", "details": "stirred for 12 h"}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "The reaction was then quenched by the addition of 10 mL of 1 N hydrochloric acid", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "EXTRACTION", "details": "extracted with dichloromethane (2\u00d730 mL)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 30.0, "units": "MILLILITER"}}, "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "The combined organic extracts were dried with magnesium sulfate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "magnesium sulfate"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "filtered"}, {"type": "CONCENTRATION", "details": "concentrated in vacuo"}, {"type": "CUSTOM", "details": "The crude residue was purified on silica (30% EtOAc/hexanes as eluent)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "crude residue"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"reaction_time": {"value": 12.0, "units": "HOUR"}, "products": [{"identifiers": [{"type": "NAME", "value": "4-(2-hydroxypropyl)-2-methoxybenzonitrile"}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A mixture of 3,4-dimethoxyphenylisocyanate (26.0 g, 145 mM) and propionamide (10.61 g, 145 mM) is heated at 160°-165° C. for 11/2 hours. A homogeneous pale yellow solution forms which after 15 minutes solidifies. The heating is discontinued and the flask is allowed to cool slowly. The mixture is triturated with acetone and this resulting white solid is filtered and dried. Yield: 32.45 g, mp 193°-197° C. ### ORD JSON:	{"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "3,4-dimethoxyphenylisocyanate"}], "amount": {"mass": {"value": 26.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "propionamide"}], "amount": {"mass": {"value": 10.61, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "is heated at 160\u00b0-165\u00b0 C. for 11/2 hours", "duration": {"value": 2.0, "units": "HOUR"}}, {"type": "TEMPERATURE", "details": "to cool slowly"}, {"type": "CUSTOM", "details": "The mixture is triturated with acetone", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "acetone"}], "reaction_role": "WORKUP"}]}}, {"type": "FILTRATION", "details": "this resulting white solid is filtered"}, {"type": "CUSTOM", "details": "dried"}], "outcomes": [{"reaction_time": {"value": 15.0, "units": "MINUTE"}, "products": [{}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: 3-(Methylsulfonyl)-5-nitro-aniline (4.3 g; 19.89 mmol) was diluted in 60 ml of ethyl acetate and a solution of potassium hydrogen carbonate (219 g, 21.87) in 10 ml of water was added. The reaction mixture was stirred at 0° C. and chloroacetylchloride (2.47 ml; 21.87 mmol) was added dropwise. The reaction mixture was allowed to reach room temperature and stirred for 2 h. Then, the phases were separated. The organic phase was dried on MgSO4 and concentrated under vacuum. The oil obtained was treated with acetone/di-isopropyl ether (1/5) and the solid obtained was filtered. 2.5 g (8.54 mmol; 43% yield) of the desired 2-Chloro-N-(3-methanesulfonyl-5-nitro-phenyl)-acetamide were obtained. ### ORD JSON:	{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "acetone di-isopropyl ether"}], "reaction_role": "REACTANT"}]}, "m1_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "3-(Methylsulfonyl)-5-nitro-aniline"}], "amount": {"mass": {"value": 4.3, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "amount": {"volume": {"value": 60.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "potassium hydrogen carbonate"}], "amount": {"mass": {"value": 219.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "chloroacetylchloride"}], "amount": {"volume": {"value": 2.47, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 0.0, "units": "CELSIUS"}}, "stirring": {"type": "CUSTOM", "details": "The reaction mixture was stirred at 0\u00b0 C."}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "to reach room temperature", "temperature": {"control": {"type": "AMBIENT"}}}, {"type": "STIRRING", "details": "stirred for 2 h", "duration": {"value": 2.0, "units": "HOUR"}}, {"type": "CUSTOM", "details": "Then, the phases were separated"}, {"type": "CUSTOM", "details": "The organic phase was dried on MgSO4"}, {"type": "CONCENTRATION", "details": "concentrated under vacuum"}, {"type": "CUSTOM", "details": "The oil obtained"}, {"type": "CUSTOM", "details": "the solid obtained"}, {"type": "FILTRATION", "details": "was filtered"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "2-Chloro-N-(3-methanesulfonyl-5-nitro-phenyl)-acetamide"}], "measurements": [{"type": "AMOUNT", "details": "AMOUNT", "amount": {"moles": {"value": 8.54, "units": "MILLIMOLE"}}}, {"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 2.5, "units": "GRAM"}}}, {"type": "YIELD", "details": "PERCENTYIELD", "percentage": {"value": 43.0}}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: Intermediate 2 was synthesized by following a similar route to Intermediate 1 using methyl 4-bromo-2-methoxybenzoate in step 1A. LCMS (ESI) m/z: 219.1 (M+H)+. ### ORD JSON:	{"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "Intermediate 1"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl 4-bromo-2-methoxybenzoate"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "Intermediate 2"}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: To a solution of 2-chloropyridine-4-methanol (1.02 g, 7.10 mmol) in 15 mL of dichloromethane was added thionyl bromide (1.77 g, 8.53 mmol) dropwise. After 15 min, the reaction was quenched with saturated aqueous ammonium chloride. The organic solution was washed 2× with water, dried over sodium sulfate, filtered, and concentrated in vacuo to provide 4-(bromomethyl)-2-chloropyridine that gave a mass ion (ES+) of 208.0 for [M+H]+. ### ORD JSON:	{"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2-chloropyridine-4-methanol"}], "amount": {"mass": {"value": 1.02, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "thionyl bromide"}], "amount": {"mass": {"value": 1.77, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 15.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "the reaction was quenched with saturated aqueous ammonium chloride", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ammonium chloride"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "The organic solution was washed 2\u00d7 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": "FILTRATION", "details": "filtered"}, {"type": "CONCENTRATION", "details": "concentrated in vacuo"}], "outcomes": [{"reaction_time": {"value": 15.0, "units": "MINUTE"}, "products": [{"identifiers": [{"type": "NAME", "value": "4-(bromomethyl)-2-chloropyridine"}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: By the procedure of Example 46, N-(2-pyrimidylmethyl)ethylenediamine is reacted with benzoyl isothiocyanate to give N-benzoyl-N'-[2-(2-pyrimidylmethylamino)-ethyl]thiourea. ### ORD JSON:	{"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "N-(2-pyrimidylmethyl)ethylenediamine"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "benzoyl isothiocyanate"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "N-benzoyl-N'-[2-(2-pyrimidylmethylamino)-ethyl]thiourea"}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A mixture of Z-α-methoxyiminopyrazineacetonitrile (4 g), acetic acid (15 ml) and 30% hydrogen peroxide in water (15 ml) was heated at a temperature of 70° C. over one night. The reaction mixture was concentrated and treated with water and chloroform. The chloroform layer was separated and dried over magnesium sulphate. Evaporation of the solvent and successive crystallization of the residue from alcohol afforded Z-α-methoxyimino-2-pyrazineacetonitrile-4-oxide, m.p. 144°-145° C. ### ORD JSON:	{"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Z-\u03b1-methoxyiminopyrazineacetonitrile"}], "amount": {"mass": {"value": 4.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "acetic acid"}], "amount": {"volume": {"value": 15.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "hydrogen peroxide"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 15.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"temperature": {"setpoint": {"value": 70.0, "units": "CELSIUS"}}, "conditions_are_dynamic": true}, "workups": [{"type": "CONCENTRATION", "details": "The reaction mixture was concentrated"}, {"type": "ADDITION", "details": "treated with water and chloroform", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "chloroform"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "The chloroform layer was separated", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "chloroform"}], "reaction_role": "WORKUP"}]}}, {"type": "DRY_WITH_MATERIAL", "details": "dried over magnesium sulphate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "magnesium sulphate"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "Evaporation of the solvent and successive crystallization of the residue from alcohol", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "alcohol"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "Z-\u03b1-methoxyimino-2-pyrazineacetonitrile-4-oxide"}], "reaction_role": "PRODUCT"}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: Steps 6 and 7: A sample of 3,3-dimethyl-1-oxo-indan-5-carbonitrile and (4′-Fluoro-3′-methyl-biphenyl-3-yl)-hydrazine hydrochloride (prepared as in example 70, steps 1 and 2 except using 3-methyl-4-fluorophenylboronic acid and 3-chloro-2-fluoroaniline as the coupling partners) are reacted together as in example 1, step 3. The crude product is then subjected to hydrolysis as in example 19, step 3 to afford 6-fluoro-7-(4-fluoro-3-methyl-phenyl)-10,10-dimethyl-5,10-dihydro-indeno[1,2-b]indole-2-carboxylic acid amide as a light yellow solid: 1H NMR (400 MHz, acetone-d6) δ 11.18 (s, 1H), 8.14 (s, 1H), 7.95 (dd, 1H, J=1.2, 7.6 Hz), 7.68 (d, 1H, J=8 Hz), 7.57 (d, 1H, J=8.4 Hz), 7.54 (dd, 1H, J=0.8, 7.6 Hz), 7.46-7.45 (m, 2H), 7.20-7.25 (m, 2H), 6.65-6.50 (br, 2H), 225 (d, 3H, J=1.6 Hz), 1.66 (s, 6H), ESMS 77/z 403.2 (M+H+). ### ORD JSON:	{"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "3-chloro-2-fluoroaniline"}], "reaction_role": "REACTANT"}]}, "m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "3,3-dimethyl-1-oxo-indan-5-carbonitrile"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "(4\u2032-Fluoro-3\u2032-methyl-biphenyl-3-yl)-hydrazine hydrochloride"}], "reaction_role": "REACTANT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "crude product"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "3-methyl-4-fluorophenylboronic acid"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "are reacted together as in example 1, step 3"}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "6-fluoro-7-(4-fluoro-3-methyl-phenyl)-10,10-dimethyl-5,10-dihydro-indeno[1,2-b]indole-2-carboxylic acid amide"}], "isolated_color": "light yellow", "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. ### Procedure: A 50 mL round bottom flask equipped with a reflux condenser was charged with solid methyl 4-amino-6-bromo-5-fluoropicolinate (1.0 g, 4.02 mmol), 2-(4-chloro-2-fluoro-3-methoxyphenyl)-1,3,2-dioxaborinane (1.227 g, 5.02 mmol), bis(triphenylphosphine)-palladium(II) dichloride (Pd(PPh3)2Cl2; 0.141 g, 0.201 mmol), and KF (0.467 g, 8.03 mmol). The reaction mixture was flushed with nitrogen, and then solvent (3:1 acetonitrile-water, 24 mL) was added. The reaction mixture was heated to reflux under nitrogen for 2 h. Upon cooling to room temperature, the product was filtered, washed with acetonitrile followed by water, and dried in a vacuum oven overnight to give the product (0.89 g) as an off-white solid: mp 204-206° C. An additional 0.29 g of product was isolated from the filtrate for a combined yield of 89%. 1H NMR (400 MHz, DMSO-d6) δ 7.54 (d, J=6.6 Hz, 1H), 7.46 (dd, J=8.5, 1.4 Hz, 1H), 7.30 (dd, J=8.4, 7.2 Hz, 1H), 6.71 (s, 2H), 3.93 (s, 3H), 3.83 (s, 3H), 3.31 (s, 4H); 13C NMR (101 MHz, DMSO-d6) δ 164.82 (s), 153.17 (d, J=249.5 Hz), 146.87 (d, J=254.3 Hz), 143.83 (dd, J=13.4, 3.8 Hz), 143.69 (d, J=4.3 Hz), 139.05 (d, J=10.6 Hz), 128.20 (d, J=3.2 Hz), 125.96 (d, J=3.4 Hz), 125.42 (d, J=3.6 Hz), 123.83 (dd, J=14.3, 3.1 Hz), 112.54 (s), 61.56 (s), 52.25 (s); 19F NMR (376 MHz, DMSO-d6) δ −129.37 (d, J=26.0 Hz), −142.56 (d, J=26.3 Hz). ### ORD JSON:	{"inputs": {"m1_m2_m4_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl 4-amino-6-bromo-5-fluoropicolinate"}], "amount": {"mass": {"value": 1.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-(4-chloro-2-fluoro-3-methoxyphenyl)-1,3,2-dioxaborinane"}], "amount": {"mass": {"value": 1.227, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "KF"}], "amount": {"mass": {"value": 0.467, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "bis(triphenylphosphine)-palladium(II) dichloride"}], "amount": {"mass": {"value": 0.141, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "conditions_are_dynamic": true}, "workups": [{"type": "CUSTOM", "details": "A 50 mL round bottom flask equipped with a reflux condenser"}, {"type": "CUSTOM", "details": "The reaction mixture was flushed with nitrogen"}, {"type": "ADDITION", "details": "solvent (3:1 acetonitrile-water, 24 mL) was added", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "acetonitrile water"}], "reaction_role": "WORKUP"}]}}, {"type": "TEMPERATURE", "details": "The reaction mixture was heated"}, {"type": "TEMPERATURE", "details": "to reflux under nitrogen for 2 h", "duration": {"value": 2.0, "units": "HOUR"}}, {"type": "FILTRATION", "details": "the product was filtered"}, {"type": "WASH", "details": "washed with acetonitrile", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "acetonitrile"}], "reaction_role": "WORKUP"}]}}, {"type": "CUSTOM", "details": "dried in a vacuum oven overnight", "duration": {"value": 8.0, "precision": 8.0, "units": "HOUR"}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "product"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 0.89, "units": "GRAM"}}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 67.4}}], "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. ### Procedure: To a solution of 1-(diisopropoxymethyl)-1H-benzo[d]imidazole (318 mg, 1.280 mmol) in THF (5 mL) at 0° C. is added LiHMDS (0.753 mL, 0.753 mmol) over 1 min. The reaction was stirred 5 min., then 3.5 mL of the 6 mL solution (1.0 theoretical equivalent of the lithium benzoimidazole) was added to a solution of tert-butyl 3-(2-(4-(ethoxycarbonyl)phenoxy)pyridin-3-yl)azetidine-1-carboxylate (300 mg, 0.753 mmol) in THF (3 mL) at 0° C. The reaction was stirred at 0° C. 30 min. LCMS showed only 5% conversion. The remaining solution of benzoimidazole was added and the reaction stirred 1 h at 0° C. LCMS shows 2:1 ratio of starting material to desired product. The reaction was quenched with 2 N HCl (15 mL) and warmed to rt and stirred overnight. The aqueous layer was neutralized with solid Na2CO3 and the aqueous layer extracted with CH2Cl2 (2×25 mL). The combined organic fractions were washed with saturated NaCl, dried (MgSO4), and concentrated. The crude material was then taken up in MeOH (3 mL) and 4.0 M HCl in dioxane was added. The reaction was stirred at rt 2 h, then concentrated to give the crude amine hydrochloride, which was taken on to the next step without purification. ### ORD JSON:	{"inputs": {"m3_m4_m5_m8": {"components": [{"identifiers": [{"type": "NAME", "value": "solution"}], "amount": {"volume": {"value": 6.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "lithium benzoimidazole"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tert-butyl 3-(2-(4-(ethoxycarbonyl)phenoxy)pyridin-3-yl)azetidine-1-carboxylate"}], "amount": {"mass": {"value": 300.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "THF"}], "amount": {"volume": {"value": 3.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "benzoimidazole"}], "reaction_role": "REACTANT"}]}, "m1_m7_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "1-(diisopropoxymethyl)-1H-benzo[d]imidazole"}], "amount": {"mass": {"value": 318.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "LiHMDS"}], "amount": {"volume": {"value": 0.753, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "THF"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "The reaction was stirred 5 min."}, "conditions_are_dynamic": true}, "workups": [{"type": "STIRRING", "details": "The reaction was stirred at 0\u00b0 C", "temperature": {"setpoint": {"value": 0.0, "units": "CELSIUS"}}}, {"type": "CUSTOM", "details": "30 min", "duration": {"value": 30.0, "units": "MINUTE"}}, {"type": "STIRRING", "details": "the reaction stirred 1 h at 0\u00b0 C", "duration": {"value": 1.0, "units": "HOUR"}, "temperature": {"setpoint": {"value": 0.0, "units": "CELSIUS"}}}], "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. ### Procedure: 4-[1-(3-Fluoro-benzyl)-2-oxo-2,3-dihydro-1H-indol-4-yl]-piperazine-1-carboxylic acid tert-butyl ester (115 mg) was dissolved in 2 mL of EtOH and 500 uL of 2.0 N HCl/EtOH was added. The solution was heated to reflux on a steam bath for 30 minutes and then cooled to room temperature. Diethyl ether was added slowly to precipitate 1-(3-Fluoro-benzyl)-4-piperazin-1-yl-1,3-dihydro-indol-2-one as a hydrochloride salt. MS: 326 (M+H)+. ### ORD JSON:	{"inputs": {"m1_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "4-[1-(3-Fluoro-benzyl)-2-oxo-2,3-dihydro-1H-indol-4-yl]-piperazine-1-carboxylic acid tert-butyl ester"}], "amount": {"mass": {"value": 115.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "EtOH"}], "amount": {"volume": {"value": 2.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "HCl EtOH"}], "amount": {"volume": {"value": 500.0, "units": "MICROLITER"}}, "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "Diethyl ether"}], "reaction_role": "REACTANT"}]}}, "conditions": {"temperature": {"control": {"type": "AMBIENT"}}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "The solution was heated"}, {"type": "TEMPERATURE", "details": "to reflux on a steam bath for 30 minutes", "duration": {"value": 30.0, "units": "MINUTE"}}, {"type": "CUSTOM", "details": "to precipitate 1-(3-Fluoro-benzyl)-4-piperazin-1-yl-1,3-dihydro-indol-2-one as a hydrochloride salt", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "1-(3-Fluoro-benzyl)-4-piperazin-1-yl-1,3-dihydro-indol-2-one"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "hydrochloride salt"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "1-(3-Fluoro-benzyl)-4-piperazin-1-yl-1,3-dihydro-indol-2-one"}]}]}]}
Below is a description of an organic reaction. Extract information from it to an ORD JSON record. ### Procedure: A mixture of 50 mg (0.143 mmol) 2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carbonitrile and 36 mg (0.143 mmol) iodine and 22 mg (0.072 mmol) silver sulfate in 1 ml acetic acid is stirred at reflux for 3 h. Then the filtrate is poured on 2N NaOH and extracted (3×) with ethyl acetate. The combined organic layers are washed with water (2×) and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (hexane:EtOAc=3:1) to afford 10 mg of the title compound as a white crystalline solid. ### ORD JSON:	{"inputs": {"m1_m2_m5_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carbonitrile"}], "amount": {"mass": {"value": 50.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "iodine"}], "amount": {"mass": {"value": 36.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "acetic acid"}], "amount": {"volume": {"value": 1.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "silver sulfate"}], "amount": {"mass": {"value": 22.0, "units": "MILLIGRAM"}}, "reaction_role": "CATALYST"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "NaOH"}], "reaction_role": "REACTANT"}]}}, "conditions": {"stirring": {"type": "CUSTOM", "details": "is stirred"}, "conditions_are_dynamic": true}, "workups": [{"type": "TEMPERATURE", "details": "at reflux for 3 h", "duration": {"value": 3.0, "units": "HOUR"}}, {"type": "EXTRACTION", "details": "extracted (3\u00d7) with ethyl acetate", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "WORKUP"}]}}, {"type": "WASH", "details": "The combined organic layers are washed with water (2\u00d7) and 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 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 flash-chromatography on silica gel (hexane:EtOAc=3:1)", "input": {"components": [{"identifiers": [{"type": "NAME", "value": "hexane"}], "reaction_role": "WORKUP"}, {"identifiers": [{"type": "NAME", "value": "EtOAc"}], "reaction_role": "WORKUP"}]}}], "outcomes": [{"products": [{"identifiers": [{"type": "NAME", "value": "title compound"}], "measurements": [{"type": "AMOUNT", "details": "MASS", "amount": {"mass": {"value": 10.0, "units": "MILLIGRAM"}}}, {"type": "YIELD", "details": "CALCULATEDPERCENTYIELD", "percentage": {"value": 14.7}}], "isolated_color": "white crystalline", "texture": {"type": "CUSTOM", "details": "solid"}, "reaction_role": "PRODUCT"}]}]}