instruction stringclasses 1
value | input stringlengths 142 4.69k | output stringlengths 235 2.08k |
|---|---|---|
Extract the chemical reaction information from the given text | The potassium salt of 4-hydroxyphenylacetic acid (9.5 g, 0.05 mL) was suspended in dimethylformamide (25 mL). Chloromethyl pivalate (7.53 g, 0.05 mol) was added and the reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was poured into ice water and extracted with ethyl acetate (100 mL)... | inputs[5]:
- identifiers[1]{type,value}:
NAME,ice water
reaction_role: REACTANT
- identifiers[1]{type,value}:
NAME,potassium
reaction_role: REACTANT
- identifiers[1]{type,value}:
NAME,4-hydroxyphenylacetic acid
reaction_role: REACTANT
amount:
type: volume
value: 0.05
... |
Extract the chemical reaction information from the given text | A mixture of benzyl 4-(2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate (697 mg, 2.12 mmol), (4-bromophenyl)(methyl)sulfane (431 mg, 2.12 mmol, Aldrich), quinolin-8-ol (61.6 mg, 0.425 mmol, Alfa Aesar), potassium carbonate (381 mg, 2.76 mmol, EMD), Copper(I) iodide (81 mg, 0.43 mmol, Alfa Aesar) in DMSO (6 mL)... | inputs[6]:
- identifiers[1]{type,value}:
NAME,"benzyl 4-(2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate"
reaction_role: REACTANT
amount:
type: mass
value: 697.0
unit: milligram
- identifiers[1]{type,value}:
NAME,(4-bromophenyl)(methyl)sulfane
reaction_role: REACTANT
... |
Extract the chemical reaction information from the given text | This example describes the preparation of disodium carboxymethyl dithiocarbamate useful as a suspressant in ore flotation processes. To a 1-Liter round bottom flask fitted with a stirrer, thermometer, reflux condenser and a dropping funnel was added 253 milliliters of water and 84.0 grams (2.1 moles) of sodium hydroxid... | inputs[7]:
- identifiers[1]{type,value}:
NAME,sodium hydroxide
reaction_role: REACTANT
amount:
type: mass
value: 84.0
unit: gram
- identifiers[1]{type,value}:
NAME,CS2
reaction_role: SOLVENT
amount:
type: mass
value: 76.14
unit: gram
- identifiers[1]{typ... |
Extract the chemical reaction information from the given text | A mixture of 4′-[(4-butyl-2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile (1.02 g), potassium carbonate (1.28 g), 4-(chloromethyl)-3,5-dimethylisoxazole (0.45 g) and N,N-dimethylformamide (20 mL) was stirred at 90° C. for 2 hr. The reaction mixture was diluted with ethyl acetate, washed with wat... | inputs[5]:
- identifiers[1]{type,value}:
NAME,"4′-[(4-butyl-2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl)methyl]biphenyl-2-carbonitrile"
reaction_role: REACTANT
amount:
type: mass
value: 1.02
unit: gram
- identifiers[1]{type,value}:
NAME,potassium carbonate
reaction_role: REACTANT
... |
Extract the chemical reaction information from the given text | (Ref.: J. Org. Chem. 2002, 67, 6226-6227) 7-Azaindole (5 g, 42.3 mmol) is added to a stirred suspension of AlCl3 (22.6 g, 169 mmol) in DCM (300 mL). After stirring at rt for 1 h, acetyl chloride (13.3 g, 169 mmol) is added drop wise and the resulting mixture is stirred for 18 h. The mixture is cooled to 00 C., quenched... | inputs[4]:
- identifiers[1]{type,value}:
NAME,7-Azaindole
reaction_role: REACTANT
amount:
type: mass
value: 5.0
unit: gram
- identifiers[1]{type,value}:
NAME,AlCl3
reaction_role: REACTANT
amount:
type: mass
value: 22.6
unit: gram
- identifiers[1]{type,va... |
Extract the chemical reaction information from the given text | N,N-dimethylformamide (15 ml), 2,4-dichlorobenzyl bromide (4.45 g) and sodium bicarbonate (1.23 g) are added to 2-benzyl-5-ethoxycarbonyl-benzimidazole (2.37 g) (example 11) and the solution is heated for one hour at 60° C. After adding ethyl acetate (70 ml) and water (70 ml) and separating the solution, the organic la... | inputs[5]:
- identifiers[1]{type,value}:
NAME,ethyl acetate
reaction_role: SOLVENT
amount:
type: volume
value: 70.0
unit: milliliter
- identifiers[1]{type,value}:
NAME,"N,N-dimethylformamide"
reaction_role: REACTANT
amount:
type: volume
value: 15.0
unit: m... |
Extract the chemical reaction information from the given text | To a stirred solution of the 2-[(2-fluorophenyl)(1-(ethoxy)ethoxy)methyl]-3-thiophenecarboxaldehyde and tetrahydrofuran (400 ml), cooled to -78° C. under nitrogen, was added, via syringe, N-methyl-4-piperidinylmagnesium chloride over 1.5 hrs. (the Grignard reagent was prepared from N-methyl-4-chloropiperidine (29.4 g) ... | inputs[6]:
- identifiers[1]{type,value}:
NAME,tetrahydrofuran
reaction_role: SOLVENT
amount:
type: volume
value: 45.0
unit: milliliter
- identifiers[1]{type,value}:
NAME,ammonium chloride
reaction_role: REACTANT
- identifiers[1]{type,value}:
NAME,ether
reaction_role: ... |
Extract the chemical reaction information from the given text | 0.511 G. of 4-Chloro-2-pyridyl isothiocyanate and 1.8 g. of n-decylisothiocyanate are combined and heated at 85° C. for 20 hours. The temperature is lowered to 75° C. and continued for 8 days. The reaction mixture is cooled, triturated with ether, filtered, washed with water and dried affording 8-chloro 3-(n-decyl) pyr... | inputs[2]:
- identifiers[1]{type,value}:
NAME,4-Chloro-2-pyridyl isothiocyanate
reaction_role: REACTANT
- identifiers[1]{type,value}:
NAME,n-decylisothiocyanate
reaction_role: REACTANT
products[1]:
- identifiers[1]{type,value}:
NAME,"8-chloro 3-(n-decyl) pyrido (1,2-a) 1,3,5-triazine-2,4-dithi... |
Extract the chemical reaction information from the given text | To a solution of N,N-dimethylformamide (5.0 mL) was added (2S)-2-[(tert-butoxycarbonyl)amino]-3-[4-(2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]propanoic acid (709.6 mg, 1.561 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (712 mg, 1.87 mmol), and N,N-diisopropylethylami... | inputs[5]:
- identifiers[1]{type,value}:
NAME,"1,2-benzenediamine"
reaction_role: REACTANT
amount:
type: mass
value: 253.0
unit: milligram
- identifiers[1]{type,value}:
NAME,"(2S)-2-[(tert-butoxycarbonyl)amino]-3-[4-(2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]propanoi... |
Extract the chemical reaction information from the given text | To a solution of γ-butyrolactone (3.0 g) in tetrahydrofuran (THF) (30 ml) was added lithium diisopronylamide (LDA) (28 ml, 1.5 M solution in cyclohexane) at -78° C. under N2, and then after 30 minutes, a solution of m-anisaldehyde (4.7 g) in THF (10 ml) was added in the solution. After being stirred for 2 hours at the ... | inputs[8]:
- identifiers[1]{type,value}:
NAME,ethyl acetate
reaction_role: SOLVENT
- identifiers[1]{type,value}:
NAME,m-anisaldehyde
reaction_role: REACTANT
amount:
type: mass
value: 4.7
unit: gram
- identifiers[1]{type,value}:
NAME,THF
reaction_role: SOLVENT
amou... |
Extract the chemical reaction information from the given text | To a stirred solution of 4-(methylthio)benzonitrile (50 g, 340 mmol) in THF (2 L) at −78° C., was added methyllithium (282 ml, 1.4 M in diethyl ether, 390 mmol) over a period of ten minutes. The solution was stirred at −78° C. For one hour and then the dry ice bath was removed. After five hours, 100 ml of water followe... | inputs[3]:
- identifiers[1]{type,value}:
NAME,4-(methylthio)benzonitrile
reaction_role: REACTANT
amount:
type: mass
value: 50.0
unit: gram
- identifiers[1]{type,value}:
NAME,methyllithium
reaction_role: REACTANT
amount:
type: volume
value: 282.0
unit: mill... |
Extract the chemical reaction information from the given text | In a round bottom flask fitted with a dean stark condenser, 3-Ethoxy-4-ethoxycarbonyl phenyl acetic acid (10.26 g, 0.0426 mol) was dissolved in toluene (100 ml) followed by slow addition of phenylboronic acid (0.494 g, 0.0040 mol) and (S)-3-methyl-1-(2-piperidinophenyl)-1-butylamine (10 g, 0.0406 mol). The reaction mix... | inputs[4]:
- identifiers[1]{type,value}:
NAME,3-Ethoxy-4-ethoxycarbonyl phenyl acetic acid
reaction_role: REACTANT
amount:
type: mass
value: 10.26
unit: gram
- identifiers[1]{type,value}:
NAME,toluene
reaction_role: SOLVENT
amount:
type: volume
value: 100.0
... |
Extract the chemical reaction information from the given text | A flask was charged with perfluorophenyl 4-(2-chloro-3′-fluoro-5-methoxy-[1,1′-biphenyl]-4-yl)quinazoline-7-sulfonate (Intermediate ZZZZZ; 0.060 g, 0.098 mmol), pyrimidin-4-amine (9.81 mg, 0.103 mmol), and THF (0.982 ml) and cooled to 0° C. LHMDS (1.0M in THF) (0.206 ml, 0.206 mmol) was added drop wise and the reaction... | inputs[4]:
- identifiers[1]{type,value}:
NAME,"perfluorophenyl 4-(2-chloro-3′-fluoro-5-methoxy-[1,1′-biphenyl]-4-yl)quinazoline-7-sulfonate"
reaction_role: REACTANT
amount:
type: mass
value: 0.06
unit: gram
- identifiers[1]{type,value}:
NAME,pyrimidin-4-amine
reaction_role: REA... |
Extract the chemical reaction information from the given text | A solution of [3-chloro-4-(3-dimethylamino-acryloyl)-phenyl]-carbamic acid tert-butyl ester (270 mg) in dioxane (3 ml) is treated with hydroxylamine hydrochloride (122 mg) and the mixture is stirred at room temperature for 10 days. The mixture is diluted with ethyl acetate, washed successively with water, 5% aqueous so... | inputs[4]:
- identifiers[1]{type,value}:
NAME,ethyl acetate
reaction_role: SOLVENT
- identifiers[1]{type,value}:
NAME,"[3-chloro-4-(3-dimethylamino-acryloyl)-phenyl]-carbamic acid tert-butyl ester"
reaction_role: REACTANT
amount:
type: mass
value: 270.0
unit: milligram
- iden... |
Extract the chemical reaction information from the given text | A suspension of methyl 4-(8-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzoate (43 mg, 0.13 mmol, 1 equiv), cyclopentyl bromide (41 μL, 0.38 mmol, 3.0 equiv) and cesium carbonate (126 mg, 0.383 mmol, 3.0 equiv) in N,N-dimethylformamide (1 mL) was heated at 100° C. After 2 h, the reaction mixture was dil... | inputs[5]:
- identifiers[1]{type,value}:
NAME,"methyl 4-(8-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzoate"
reaction_role: REACTANT
amount:
type: mass
value: 43.0
unit: milligram
- identifiers[1]{type,value}:
NAME,cyclopentyl bromide
reaction_role: REACTANT
... |
Extract the chemical reaction information from the given text | To a stirred solution of N-(4-chlorophenyl)-2-(2-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yloxy)acetyl)hydrazinecarbothioamide (0.2 g, 0.49 mmol) in dry DMF (10 mL) at room temperature, EDC HCl (0.189 g, 0.98 mmol) and TEA (0.148 g 1.4 6 mmol) were added. The reaction was stirred at room temperature overnight and monitored ... | inputs[4]:
- identifiers[1]{type,value}:
NAME,"N-(4-chlorophenyl)-2-(2-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yloxy)acetyl)hydrazinecarbothioamide"
reaction_role: REACTANT
amount:
type: mass
value: 0.2
unit: gram
- identifiers[1]{type,value}:
NAME,EDC HCl
reaction_role: REACTANT
... |
Extract the chemical reaction information from the given text | 4-(4-Fluorobenzyl)-N-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidin-2-amine (103 mg, 0.24 mmol) was dissolved in DCM (3 mL). mCPBA (61.8 mg, 0.36 mmol) was added and the reaction was stirred at rt for 2 h. Water was added and the product was obtained by separating the organic phase and ... | inputs[3]:
- identifiers[1]{type,value}:
NAME,"4-(4-Fluorobenzyl)-N-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidin-2-amine"
reaction_role: REACTANT
amount:
type: mass
value: 103.0
unit: milligram
- identifiers[1]{type,value}:
NAME,DCM
reaction_r... |
Extract the chemical reaction information from the given text | Under nitrogen atmosphere 16.76 g of (±)-(3RS,4SR)-3-(3,4-dimethoxyphenyl)-4-nitrocyclohexanone (compound F1) are dissolved in 300 ml of tetrahydrofurane, the solution is cooled to −78° C., and 75 ml of 1 M solution of potassium tri-sec-butylborohydride in tetrahydrofurane is added dropwise. After stirring for further ... | inputs[7]:
- identifiers[1]{type,value}:
NAME,phosphate
reaction_role: REACTANT
- identifiers[1]{type,value}:
NAME,"(±)-(3RS,4SR)-3-(3,4-dimethoxyphenyl)-4-nitrocyclohexanone"
reaction_role: REACTANT
amount:
type: mass
value: 16.76
unit: gram
- identifiers[1]{type,value}:
... |
Extract the chemical reaction information from the given text | To a solution of 6-methoxynicotinic acid (100 mg, 0.65 mmol) in SOCK, (2 mL) was added DMF (1 drop). The mixture was stirred at 60° C. for 20 min. The volatiles were removed in vacuo to give 6-methoxynicotinoyl chloride, which was used for the next step directly. To a suspension of N4-(3-(difluoromethoxy)phenyl)-2-(pyr... | inputs[4]:
- identifiers[1]{type,value}:
NAME,6-methoxynicotinoyl chloride
reaction_role: REACTANT
- identifiers[1]{type,value}:
NAME,THF
reaction_role: SOLVENT
amount:
type: volume
value: 5.0
unit: milliliter
- identifiers[1]{type,value}:
NAME,"N4-(3-(difluoromethoxy)phe... |
Extract the chemical reaction information from the given text | A microwave vial was charged with 3-fluoro-4-methylphenylboronic acid (0.058 g, 0.38 mmol), 4-chloro-N-(4-(2-(trimethylsilyl)furo[3,2-b]pyridin-7-ylthio)phenyl)phthalazin-1-amine (0.090 g, 0.19 mmol), and sodium carbonate (2.0 M in H2O) (0.38 ml, 0.75 mmol) and dissolved in toluene (1.5 mL) and water (0.2 mL). Pd(Ph3P)... | inputs[6]:
- identifiers[1]{type,value}:
NAME,TBAF
reaction_role: REACTANT
amount:
type: volume
value: 0.23
unit: milliliter
- identifiers[1]{type,value}:
NAME,3-fluoro-4-methylphenylboronic acid
reaction_role: REACTANT
amount:
type: mass
value: 0.058
unit... |
Extract the chemical reaction information from the given text | Under an atmosphere of argon, tert-butyllithium (1.7 M in pentane) (0.576 mL, 0.98 mmol) was added dropwise to anhydrous tetrahydrofuran (4.00 mL) at −100° C. 4-Bromo-2-cyclopropylpyridine (0.097 g, 0.49 mmol) in anhydrous THF (2.00 mL) was added dropwise to the mixture. The solution was stirred for 2 minutes before dr... | inputs[7]:
- identifiers[1]{type,value}:
NAME,hydrogen chloride
reaction_role: REACTANT
amount:
type: volume
value: 1.176
unit: milliliter
- identifiers[1]{type,value}:
NAME,MeOH
reaction_role: SOLVENT
amount:
type: volume
value: 2.0
unit: milliliter
- i... |
Extract the chemical reaction information from the given text | 4-Bromo-2-methylquinoline (53a) (1.0 g, 4.5 mmol) was dissolved in 10 mL of anhydrous THF and the resulting solution was cooled down to −78° C. A solution of n-BuLi (3.0 mL, 1.6M, 4.8 mmol) was added slowly and the resulting solution was maintained at −78° C. for 5 min. Meanwhile, in another flask methyl 4-formylbenzoa... | inputs[5]:
- identifiers[1]{type,value}:
NAME,lithium
reaction_role: REACTANT
- identifiers[1]{type,value}:
NAME,n-BuLi
reaction_role: REACTANT
amount:
type: volume
value: 3.0
unit: milliliter
- identifiers[1]{type,value}:
NAME,4-Bromo-2-methylquinoline
reaction_role:... |
Extract the chemical reaction information from the given text | Ethylene diamine (130 mg, 2.1 mmol) and triethylamine (510 mg, 5.0 mmol), together dissolved in 10 mL anhydrous ether is added to pentafluorobenzoyl chloride (1.2 g, 5.0 mmol) in 10 mL anhydrous ether. White precipitate is obtained and filtered off. The residue is washed with chloroform, then water and then filtered to... | inputs[3]:
- identifiers[1]{type,value}:
NAME,Sodium azide
reaction_role: REACTANT
amount:
type: mass
value: 270.0
unit: milligram
- identifiers[1]{type,value}:
NAME,III
reaction_role: REACTANT
amount:
type: mass
value: 870.0
unit: milligram
- identifier... |
Extract the chemical reaction information from the given text | To a suspension of 4.70 g of lithium aluminium hydride in 250 ml of dried tetrahydrofuran, a solution of 47.7 g of 4-azidomethyl-N-triphenylmethylpiperidine in 250 ml of dried tetrahydrofuran was added dropwise under ice-cooling, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was adde... | inputs[4]:
- identifiers[1]{type,value}:
NAME,sodium hydroxide
reaction_role: REACTANT
- identifiers[1]{type,value}:
NAME,tetrahydrofuran
reaction_role: SOLVENT
- identifiers[1]{type,value}:
NAME,lithium aluminium hydride
reaction_role: REACTANT
amount:
type: mass
value: 4.... |
Extract the chemical reaction information from the given text | 3-Hydroxy-4,4-dimethyl-5α-chola-8,14-dien-24-oic acid ethyl ester (1.9 g) is suspended in a mixture of 190 ml of 96% ethanol and 63 ml of 1M sodium hydroxide. The mixture is stirred for 3.5 h at room temperature. After aqueous work-up and crystallization from ethanol/water, the title compound (1.48 g) is isolated. 1H-N... | inputs[3]:
- identifiers[1]{type,value}:
NAME,"3-Hydroxy-4,4-dimethyl-5α-chola-8,14-dien-24-oic acid ethyl ester"
reaction_role: REACTANT
amount:
type: mass
value: 1.9
unit: gram
- identifiers[1]{type,value}:
NAME,ethanol
reaction_role: SOLVENT
amount:
type: volume
... |
Extract the chemical reaction information from the given text | To a solution of Example 1A (780 mg, 2.5 mmol) and 5-chloro-2-methoxy-benzoyl chloride (515 mg, 2.5 mmol) in CH2Cl2 (25 mL) under N2 atmosphere at 0° C. was added 4-dimethylaminopyridine (DMAP) (1.22 g. 10 mmol) and the mixture was allowed to warm to room temperature. The mixture was stirred for 20 hours, washed sequen... | inputs[3]:
- identifiers[1]{type,value}:
NAME,5-chloro-2-methoxy-benzoyl chloride
reaction_role: REACTANT
amount:
type: mass
value: 515.0
unit: milligram
- identifiers[1]{type,value}:
NAME,CH2Cl2
reaction_role: SOLVENT
amount:
type: volume
value: 25.0
unit... |
Extract the chemical reaction information from the given text | To a solution of methanesulfonyl chloride (0.31 mL, 4.07 mmol) in acetonitrile (10 mL) was added dropwise a mixture of 3-chloro-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acid (i.e. the carboxylic acid product of Example 3, Step D) (1.0 g, 3.87 mmol) and triethylamine (0.54 mL, 3.87 mmol) in acetonitrile (5 mL) ... | inputs[6]:
- identifiers[1]{type,value}:
NAME,methanesulfonyl chloride
reaction_role: REACTANT
amount:
type: volume
value: 0.31
unit: milliliter
- identifiers[1]{type,value}:
NAME,3-chloro-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acid
reaction_role: REACTANT
- identi... |
Extract the chemical reaction information from the given text | To 130 (2.285g, 5 mmol) in dry methanol (10 mL) was added HCl (5 mL, 5 mmol, 1 M in diethyl ether) and stirred at room temperature for about 1 hour. The reaction was evaporated in vacuo, dissolved in water, filtered, evaporated and then dried under vacuum overnight to afford a solid 164 (2.396 g, 97%), mp 131–133° C.; ... | inputs[3]:
- identifiers[1]{type,value}:
NAME,"130"
reaction_role: REACTANT
amount:
type: mass
value: 2.285
unit: gram
- identifiers[1]{type,value}:
NAME,HCl
reaction_role: REACTANT
amount:
type: volume
value: 5.0
unit: milliliter
- identifiers[1]{type,v... |
Extract the chemical reaction information from the given text | To a reaction mixture containing the (Z)-styryl 2-hydroxyphenylsulfide (5 mmol), anhydrous pyridine (5 mmol) and acetic anhydride (5 mmol) in dry chloroform (10 ml) is stirred for 5 hours at room temperature (22° C.). The reaction mixture is then diluted with water (20 ml) and shaken well in a separating funnel. The lo... | inputs[4]:
- identifiers[1]{type,value}:
NAME,(Z)-styryl 2-hydroxyphenylsulfide
reaction_role: REACTANT
amount:
type: moles
value: 5.0
unit: millimole
- identifiers[1]{type,value}:
NAME,pyridine
reaction_role: REACTANT
amount:
type: moles
value: 5.0
unit: ... |
Extract the chemical reaction information from the given text | An ethanol solution (100 ml) of the 9.89 g of the 2'-acetoxy-4,4',6'-tris(methoxymethoxy)-3'-(3-methyl-2-butenyl)chalcone obtained as the intermediate in Specific Example 18 was added into a suspension of 5.0 g of 5% palladium/carbon in 70 ml of ethanol, in which a hydrogen gas had been sufficiently absorbed in advance... | inputs[4]:
- identifiers[1]{type,value}:
NAME,"2'-acetoxy-4,4',6'-tris(methoxymethoxy)-3'-(3-methyl-2-butenyl)chalcone"
reaction_role: REACTANT
amount:
type: mass
value: 9.89
unit: gram
- identifiers[1]{type,value}:
NAME,ethanol
reaction_role: SOLVENT
amount:
type: vo... |
Extract the chemical reaction information from the given text | A solution of 3-(6-(methoxycarbonyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinolin-2-yl)benzoic acid (330 mg, 0.88 mmol) and 1,1′-carbonyldiimidazole (500 mg, 3.08 mmol) in tetrahydrofuran (6 mL) was heated to 60° C. for 2 h, then was cooled to room temperature and treated with pyrazin-2-amine (92.2 mg, 0.97 mmol,). After st... | inputs[8]:
- identifiers[1]{type,value}:
NAME,ethyl acetate
reaction_role: SOLVENT
- identifiers[1]{type,value}:
NAME,"3-(6-(methoxycarbonyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinolin-2-yl)benzoic acid"
reaction_role: REACTANT
amount:
type: mass
value: 330.0
unit: milligram
- i... |
Extract the chemical reaction information from the given text | To a solution of 4-methoxy-2-nitrobenzoic acid (10.0 g, 50.7 mmol) in DMF (200 mL) at 0° C. was added DBU (15.2 mL, 101 mmol) followed by iodomethane (9.47 mL, 152 mmol). The reaction mixture was allowed to stir at 0° C. for 15 min then at rt overnight. The mixture was poured into water and extracted with EtOAc. The or... | inputs[4]:
- identifiers[1]{type,value}:
NAME,iodomethane
reaction_role: REACTANT
amount:
type: volume
value: 9.47
unit: milliliter
- identifiers[1]{type,value}:
NAME,4-methoxy-2-nitrobenzoic acid
reaction_role: REACTANT
amount:
type: mass
value: 10.0
unit... |
Extract the chemical reaction information from the given text | A mixture of 2-(1-methyl-piperidin-4-ylmethyl)-benzoic acid methyl ester (97 mg; 0.39 mmol; 1 eq.) and 5M NaOH (2 mL) in EtOH (3 mL) was stirred at 60° C. for 4 hours. After cooling down, the solution was neutralised with 1M HCl and freeze dried to afford the title compound as a white solid which was used without furth... | inputs[4]:
- identifiers[1]{type,value}:
NAME,2-(1-methyl-piperidin-4-ylmethyl)-benzoic acid methyl ester
reaction_role: REACTANT
amount:
type: mass
value: 97.0
unit: milligram
- identifiers[1]{type,value}:
NAME,NaOH
reaction_role: REACTANT
amount:
type: volume
... |
Extract the chemical reaction information from the given text | 4-Chloro-6,7-dimethoxyquinoline (56.1 mg), 5-bromo-2-hydroxybenzophenone (361 mg), and 4-dimethylaminopyridine (168 mg) were suspended in o-dichlorobenzene (5 ml), and the suspension was stirred at 160° C. for 7 hr. The reaction solution was cooled to room temperature, and the solvent was then removed therefrom by dist... | inputs[4]:
- identifiers[1]{type,value}:
NAME,o-dichlorobenzene
reaction_role: SOLVENT
amount:
type: volume
value: 5.0
unit: milliliter
- identifiers[1]{type,value}:
NAME,"4-Chloro-6,7-dimethoxyquinoline"
reaction_role: REACTANT
amount:
type: mass
value: 56.1
... |
Extract the chemical reaction information from the given text | To a mixture of isopropyl 4,5-dichloro-6-(4-methoxyphenyl)picolinate (5.25 g, 15.4 mmol) in tetrahydrofuran (40 mL) and water (10 mL) was added potassium hydroxide (1.26 g, 22.4 mmol). The reaction mixture was allowed to stir at room temperature for 12 h. After 1 hour of stirring, solids precipitated from the mixture. ... | inputs[3]:
- identifiers[1]{type,value}:
NAME,"isopropyl 4,5-dichloro-6-(4-methoxyphenyl)picolinate"
reaction_role: REACTANT
amount:
type: mass
value: 5.25
unit: gram
- identifiers[1]{type,value}:
NAME,tetrahydrofuran
reaction_role: SOLVENT
amount:
type: volume
... |
Extract the chemical reaction information from the given text | To a solution of (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(3-hydroxypropanoyloxy)ethyl)pyridine 1-oxide (0.311 g, 0.632 mmol), 4-(N-(tert-butoxycarbonyl)methylsulfonamido)-3-(cyclopropylmethoxy)benzoic acid (0.243 g, 0.632 mmol), and EDC (0.363 g, 1.895 mmol) in dry DCM (15 ml), DMAP (... | inputs[5]:
- identifiers[1]{type,value}:
NAME,"(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(3-hydroxypropanoyloxy)ethyl)pyridine 1-oxide"
reaction_role: REACTANT
amount:
type: mass
value: 0.311
unit: gram
- identifiers[1]{type,value}:
NAME,4-(N-(tert-... |
Extract the chemical reaction information from the given text | A 1000 ml 3-neck round bottom flask, fitted with an overhead stirrer, was charged with 5,7-difluoro-2,3-dihydro-1H-indene-1-one (10 g, 59.4 mmol) followed by dry dichloromethane (100 ml) and methanesulfonic acid (71.3 ml, 1.1 mol). The reaction was cooled to 0° C. (ice bath) and to this was added sodium azide (5.41 g; ... | inputs[7]:
- identifiers[1]{type,value}:
NAME,"5,7-difluoro-2,3-dihydro-1H-indene-1-one"
reaction_role: REACTANT
amount:
type: mass
value: 10.0
unit: gram
- identifiers[1]{type,value}:
NAME,aqueous solution
reaction_role: REACTANT
- identifiers[1]{type,value}:
NAME,sodium... |
Extract the chemical reaction information from the given text | Cis-{3-[4-(2-Oxo-2H-pyridin-1-yl)-benzoylamino]-piperidin-4-yl}-carbamic acid benzyl ester (0.26 mmol) was dissolved in CH3CN (1.5 ml). Iodoisopropane (0.04 mL) was added, followed by the addition of Na2CO3 (70 mg). The resulting mixture was stirred at 80° C. overnight. After cooling, it was extracted with EtOAc (3×), ... | inputs[4]:
- identifiers[1]{type,value}:
NAME,"Cis-{3-[4-(2-Oxo-2H-pyridin-1-yl)-benzoylamino]-piperidin-4-yl}-carbamic acid benzyl ester"
reaction_role: REACTANT
amount:
type: moles
value: 0.26
unit: millimole
- identifiers[1]{type,value}:
NAME,CH3CN
reaction_role: REACTANT
... |
Extract the chemical reaction information from the given text | To a solution of tert-butyl (2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)acetate (130 mg, 0.52 mmol, described in Intermediate 7) in DMF (0.7 mL) was added sodium hydride (15 mg of a 60% dispersion in mineral oil, 0.38 mmol). The mixture was stirred for 5 min, then 4,6-dichloropyrimidine (234 mg, 1.57 mmol) was added and ar... | inputs[5]:
- identifiers[1]{type,value}:
NAME,"4,6-dichloropyrimidine"
reaction_role: REACTANT
amount:
type: mass
value: 234.0
unit: milligram
- identifiers[1]{type,value}:
NAME,"tert-butyl (2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)acetate"
reaction_role: REACTANT
amount:
... |
Extract the chemical reaction information from the given text | A mixture of ethyl 3-[2-({7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}carbonyl)hydrazino]-3-oxopropanoate (0.96 g), Lawesson's reagent (0.97 g) and tetrahydrofuran (20 mL) was stirred at 50° C. for 2 hr. The reaction mixture was concentrated, and the residue was subjected to silica gel column chromatography, and t... | inputs[3]:
- identifiers[1]{type,value}:
NAME,"ethyl 3-[2-({7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}carbonyl)hydrazino]-3-oxopropanoate"
reaction_role: REACTANT
amount:
type: mass
value: 0.96
unit: gram
- identifiers[1]{type,value}:
NAME,Lawesson's reagent
reaction_rol... |
Extract the chemical reaction information from the given text | 1-Benzyl-3-oxo-azetidine (1.6 g, 10 mmol, 1.0 equiv), prepared as described in the literature (Katritzky, A. R.; Cundy, D. J.; J. Heterocyclic Chem. 1994, 31 271-275), was dissolved in dry MeOH and the solution was cooled to −78° C. Gaseous ammonia was was bubbled through the solution for 30 mins at which time 3 angstr... | inputs[5]:
- identifiers[1]{type,value}:
NAME,1-Benzyl-3-oxo-azetidine
reaction_role: REACTANT
amount:
type: mass
value: 1.6
unit: gram
- identifiers[1]{type,value}:
NAME,Heterocyclic
reaction_role: REACTANT
- identifiers[1]{type,value}:
NAME,KCN
reaction_role: REACTA... |
Extract the chemical reaction information from the given text | To a stirred solution of compound 247d (1.9 g, 9.6 mmol) in dry DMF (25 mL) was added K2CO3 (1.32 g, 9.6 mmol) at room temperature. The reaction mixture was stirred for 30 min and methyl iodide (0.77 mL, 12.4 mmol) was added. After 2 hrs at room temperature, 5% aqueous citric acid was added. The mixture was extracted w... | inputs[5]:
- identifiers[1]{type,value}:
NAME,citric acid
reaction_role: REACTANT
- identifiers[1]{type,value}:
NAME,methyl iodide
reaction_role: REACTANT
amount:
type: volume
value: 0.77
unit: milliliter
- identifiers[1]{type,value}:
NAME,compound 247d
reaction_role:... |
Extract the chemical reaction information from the given text | N-Carbobenzyloxy-L-aspartic anhydride (1 mmol) was dissolved in 50 mL methylene chloride, followed by the addition of 1.05 eq of dodecylamine and 1.1 eq of triethylamine. The reaction was capped to prevent evaporation, and stirred for 12 hours. When no trace of starting material could be detected by thin layer chromato... | inputs[4]:
- identifiers[1]{type,value}:
NAME,N-Carbobenzyloxy-L-aspartic anhydride
reaction_role: REACTANT
amount:
type: moles
value: 1.0
unit: millimole
- identifiers[1]{type,value}:
NAME,methylene chloride
reaction_role: SOLVENT
amount:
type: volume
value: 50... |
Extract the chemical reaction information from the given text | 5-(2-Fluoropyridin-3-yl)-1H-pyrrole-3-carbaldehyde (610 mg) was dissolved in N,N-dimethylformamide (20 mL), N-chlorosuccinimide (641 mg) was added, and the mixture was stirred at 80° C. for 40 min. After cooling the reaction mixture, water was added, and the mixture was extracted with ethyl acetate. The extract was was... | inputs[3]:
- identifiers[1]{type,value}:
NAME,5-(2-Fluoropyridin-3-yl)-1H-pyrrole-3-carbaldehyde
reaction_role: REACTANT
amount:
type: mass
value: 610.0
unit: milligram
- identifiers[1]{type,value}:
NAME,"N,N-dimethylformamide"
reaction_role: SOLVENT
amount:
type: vol... |
Extract the chemical reaction information from the given text | Tetrabromomethane (24.82 g, 0.747 mole) and triphenylphosphine (39.17 g, 0.149 mole) were stirred together in dry methylene chloride (100 mL) for 5 min. at 0° C. under a nitrogen atmosphere. To this mixture was added dropwise pyridine 3-carboxaldehyde (4 g, 0.0373 mole). The solution was then stirred for 45 min. at amb... | inputs[4]:
- identifiers[1]{type,value}:
NAME,Tetrabromomethane
reaction_role: REACTANT
amount:
type: mass
value: 24.82
unit: gram
- identifiers[1]{type,value}:
NAME,triphenylphosphine
reaction_role: REACTANT
amount:
type: mass
value: 39.17
unit: gram
- ... |
Extract the chemical reaction information from the given text | To a solution of 2-(4-(2,4-difluorobenzyl)piperazin-1-yl)-N-isopropyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-3-amine (50 mg, 0.124 mmol) and DIPEA (0.032 mL, 0.186 mmol) in DCM (1 mL) was added isobutyryl chloride (0.013 mL, 0.124 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 1 h, warmed to 23° C. and st... | inputs[4]:
- identifiers[1]{type,value}:
NAME,"2-(4-(2,4-difluorobenzyl)piperazin-1-yl)-N-isopropyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-3-amine"
reaction_role: REACTANT
amount:
type: mass
value: 50.0
unit: milligram
- identifiers[1]{type,value}:
NAME,DIPEA
reaction_role: REA... |
Extract the chemical reaction information from the given text | Thionyl chloride (6 ml) was added to 5,6-dichloronicotinic acid (600 mg, 3.13 mmol), and stirred under a nitrogen atmosphere at 90° C. for 30 minutes. The reaction solution was concentrated under reduced pressure, and with cooling with ice, triethylamine (1.31 ml, 9.38 mmol) and N-methyl-2-pyrrolidin-1-ylethanamine (48... | inputs[6]:
- identifiers[1]{type,value}:
NAME,tetrahydrofuran
reaction_role: SOLVENT
amount:
type: volume
value: 4.0
unit: milliliter
- identifiers[1]{type,value}:
NAME,chloroform
reaction_role: SOLVENT
- identifiers[1]{type,value}:
NAME,Thionyl chloride
reaction_role... |
Extract the chemical reaction information from the given text | 4-Hydroxy-4-piperidinecarboxylic acid hydrochloride salt (1 g, 5.1 mmol) was added to a 2% hydrochloric acid solution in methanol (25 mL) and the mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure to give the title compound as the hydrochloride salt (1 g, 92%) as a white s... | inputs[3]:
- identifiers[1]{type,value}:
NAME,4-Hydroxy-4-piperidinecarboxylic acid hydrochloride salt
reaction_role: REACTANT
amount:
type: mass
value: 1.0
unit: gram
- identifiers[1]{type,value}:
NAME,hydrochloric acid
reaction_role: REACTANT
- identifiers[1]{type,value}:
... |
Extract the chemical reaction information from the given text | 1-[2-((R)-4-tert-Butoxycarbonyl-3-methyl-piperazin-1-yl)-acetyl]-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester (200 mg, 0.48 mmol) was dissolved in 2.0 M methylamine in MeOH (2.4 mL) and heated under microwave irradiation at 120° C. for 4 h. The solvent was removed in vacuo and the resulting oil was purified by ... | inputs[3]:
- identifiers[1]{type,value}:
NAME,"1-[2-((R)-4-tert-Butoxycarbonyl-3-methyl-piperazin-1-yl)-acetyl]-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester"
reaction_role: REACTANT
amount:
type: mass
value: 200.0
unit: milligram
- identifiers[1]{type,value}:
NAME,methylami... |
Extract the chemical reaction information from the given text | A solution of allyl-(2-iodo-4-methanesulfonyl-phenyl)-amine (1.43 g, 4.1 mmol) in DMF (20 mL) is treated with n-Bu4NCl (1.47 g, 5.32 mmol), Pd(OAc)2 (56.6 mg, 0.2 mmol), and stirred at 100° C. for 1 h. HCl (5.3 mL, 3 M) is added, and the mixture is cooled to rt, filtered through a pad of Celite, and extracted with EtOA... | inputs[5]:
- identifiers[1]{type,value}:
NAME,allyl-(2-iodo-4-methanesulfonyl-phenyl)-amine
reaction_role: REACTANT
amount:
type: mass
value: 1.43
unit: gram
- identifiers[1]{type,value}:
NAME,DMF
reaction_role: SOLVENT
amount:
type: volume
value: 20.0
uni... |
Extract the chemical reaction information from the given text | To a solution of ethyl 4-[2-[(2-bromo-4-methylphenyl)amino]-4-chloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]butanoate (1.42 g, 2.74 mmol) in tetrahydrofuran (15.0 mL) was added lithium borohydride (178.7 mg, 8.20 mmol) at 0° C. The reaction mixture was stirred at room temperature for 24 hr. The reaction mixture was que... | inputs[3]:
- identifiers[1]{type,value}:
NAME,"ethyl 4-[2-[(2-bromo-4-methylphenyl)amino]-4-chloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]butanoate"
reaction_role: REACTANT
amount:
type: mass
value: 1.42
unit: gram
- identifiers[1]{type,value}:
NAME,lithium borohydride
reaction... |
Extract the chemical reaction information from the given text | To a solution of ethyl 3-(dimethylamino)-2-(2,4,5-trifluorobenzoyl)acrylate (64 g, 212 mmol) in a mixed solvent of Ethanol (150 mL)/Diethyl ether (300 mL) was added tert-Butylamine (44.6 mL, 425 mmol), and the reaction mixture was stirred at rt for 2 h. The mixture was concentrated under reduced pressure, the resulting... | inputs[5]:
- identifiers[1]{type,value}:
NAME,potassium carbonate
reaction_role: REACTANT
amount:
type: mass
value: 88.0
unit: gram
- identifiers[1]{type,value}:
NAME,"ethyl 3-(dimethylamino)-2-(2,4,5-trifluorobenzoyl)acrylate"
reaction_role: REACTANT
amount:
type: ma... |
Extract the chemical reaction information from the given text | To a solution of 7-hydroxy-7,11,15,19-tetramethyleicosane-2,4-dione (72.5 g) and dimethyl acetonedicarboxylate (29.6 g) in methanol (190 ml) at 0° was added a solution of sodium methoxide in methanol (from 2.44 g of sodium and 90 ml of methanol). The solution was stirred at room temperature for 44 hr and was concentrat... | inputs[4]:
- identifiers[1]{type,value}:
NAME,"7-hydroxy-7,11,15,19-tetramethyleicosane-2,4-dione"
reaction_role: REACTANT
amount:
type: mass
value: 72.5
unit: gram
- identifiers[1]{type,value}:
NAME,dimethyl acetonedicarboxylate
reaction_role: REACTANT
amount:
type: ... |
Extract the chemical reaction information from the given text | To a stirred, ice-cold solution of 7.75 g. of ethyl-7-carboxy-2-phenylthioheptanoate in 25 ml. of dichloromethane is added 3.5 ml. of trifluoroacetic anhydride during 2 minutes. The solution is stirred at ambient temperature for 10 minutes, recooled to 0° C. and treated with 9 ml. of furan during 2 minutes. The resulti... | inputs[4]:
- identifiers[1]{type,value}:
NAME,dichloromethane
reaction_role: SOLVENT
- identifiers[1]{type,value}:
NAME,ethyl-7-carboxy-2-phenylthioheptanoate
reaction_role: REACTANT
- identifiers[1]{type,value}:
NAME,trifluoroacetic anhydride
reaction_role: REACTANT
- identifiers[1]{typ... |
Extract the chemical reaction information from the given text | A solution of NaOH (1.44 g, 36.0 mmol) in H2O (15.0 g) was added at 20-25° C. over 5 min to a mixture of Boc-Leu-Leu-Lys(Z)-Leu-Leu-OMe (SEQ. ID No. 2) (12.0 g, 14.16 mmol) THF (48.0 g) and H2O (18.0 g). The resulting mixture was stirred for 2 h. 98% Formic acid (5 g) was added, followed by ethyl acetate (30.0 g). The ... | inputs[5]:
- identifiers[1]{type,value}:
NAME,Formic acid
reaction_role: REACTANT
amount:
type: mass
value: 5.0
unit: gram
- identifiers[1]{type,value}:
NAME,ethyl acetate
reaction_role: SOLVENT
amount:
type: mass
value: 30.0
unit: gram
- identifiers[1]{... |
Extract the chemical reaction information from the given text | A suspension of 2-(3-(4-(1H-indazol-5-ylamino)quinazolin-2-yl)phenoxy)acetic acid (70 mg, 0.14 mmol), PyBOP® (40 mg, 0.077 mmol), DIEA (24 μL, 0.14 mmol) in dry CH2Cl2:DMF (2:0.1 mL) was stirred at RT for 15 minutes. To this solution of activated acid was added 2,2,2-trifluoroethanamine (9.0 mg, 0.091 mmol). After 30 m... | inputs[6]:
- identifiers[1]{type,value}:
NAME,"2,2,2-trifluoroethanamine"
reaction_role: REACTANT
amount:
type: mass
value: 9.0
unit: milligram
- identifiers[1]{type,value}:
NAME,DIEA
reaction_role: REACTANT
- identifiers[1]{type,value}:
NAME,PyBOP
reaction_role: REAC... |
Extract the chemical reaction information from the given text | A mixture of trans-2-[-3-(2-hydroxy-n-propylsulfonyl)-4-n-propoxy-5-(4-bromobutoxy)phenyl]-5-(3,4,5-trimethoxyphenyl) tetrahydrofuran (64 mg, 0.10 mmol)(Example 19C), imidazole (27 mg, 0.40 mmol) and potassium carbonate (55 mg, 0.40 mmol) in acetone (3 mL) was heated with stirring at 60° C. under nitrogen for 24 h. The... | inputs[4]:
- identifiers[1]{type,value}:
NAME,"trans-2-[-3-(2-hydroxy-n-propylsulfonyl)-4-n-propoxy-5-(4-bromobutoxy)phenyl]-5-(3,4,5-trimethoxyphenyl) tetrahydrofuran"
reaction_role: REACTANT
amount:
type: mass
value: 64.0
unit: milligram
- identifiers[1]{type,value}:
NAME,imidazo... |
Extract the chemical reaction information from the given text | A solution of (1S,9S) 6,10-dioxo-1,2,3,4,7,8,9,10-octahydro-9-(benzoylamino)-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid (212e) (345 mg, 1.0 mmol), (4S) t-butyl N-(allyloxycarbonyl)-4-amino-5-oxopentanoate semicarbazone (208a) (361 mg, 1.1 mmol, 1.1 equiv) and (Ph3P)2PdCl2 (20 mg) in CH2Cl2 (5 ml), was treated... | inputs[8]:
- identifiers[1]{type,value}:
NAME,1-hydroxybenzotriazole
reaction_role: REACTANT
amount:
type: mass
value: 297.0
unit: milligram
- identifiers[1]{type,value}:
NAME,"(1S,9S) 6,10-dioxo-1,2,3,4,7,8,9,10-octahydro-9-(benzoylamino)-6H-pyridazino[1,2-a][1,2]diazepine-1-carbo... |
Extract the chemical reaction information from the given text | A 2 L dry round bottom flask was charged with 1-bromo-2-fluoro-4-methyl-5-nitrobenzene (24.5 g, 0.1 mol, 97%), DMF-DIPA (39 g, 0.22 mol), Et3N (16 mL, 0.11 mol) and dry DMF (100 mL). The mixture was stirred at 130° C. for 2 h. After removal of the volatiles the residue was dissolved in a mixture of toluene (650 mL) and... | inputs[5]:
- identifiers[1]{type,value}:
NAME,1-bromo-2-fluoro-4-methyl-5-nitrobenzene
reaction_role: REACTANT
amount:
type: mass
value: 24.5
unit: gram
- identifiers[1]{type,value}:
NAME,DMF-DIPA
reaction_role: REACTANT
amount:
type: mass
value: 39.0
unit... |
Extract the chemical reaction information from the given text | Into a 40 mL septum-cap vial were added sodium tert-butoxide (68 mg, 0.71 mmol), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (28 mg, 0.07 mmol), and Pd2(dba)3 (0.03 mmol). The vial was sealed and evacuated/purged 5× with nitrogen. A solution of 6-((S)-3-benzyl-piperazin-1-yl)-1-cyclobutyl-3-ethyl-1H-indazole... | inputs[6]:
- identifiers[1]{type,value}:
NAME,sodium tert-butoxide
reaction_role: REACTANT
amount:
type: mass
value: 68.0
unit: milligram
- identifiers[1]{type,value}:
NAME,"2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl"
reaction_role: REACTANT
amount:
type: ... |
Extract the chemical reaction information from the given text | A 20% solution of phosgene in toluene (715 μl) was added to a stirred and cooled solution of N-(2-amino-4-methyl-3-thienylsulfonyl)-N′-isopropylthiourea (0.22 g) and triethylamine (313 μl) in dry THF (5 ml) the temperature being kept below 5° C. After stirring for 1.5 h the mixture was evaporated and triturated with 10... | inputs[6]:
- identifiers[1]{type,value}:
NAME,N-(2-amino-4-methyl-3-thienylsulfonyl)-N′-isopropylthiourea
reaction_role: REACTANT
amount:
type: mass
value: 0.22
unit: gram
- identifiers[1]{type,value}:
NAME,triethylamine
reaction_role: REACTANT
amount:
type: volume
... |
Extract the chemical reaction information from the given text | 1,4-dioxa-8-azaspiro[4.5]decane (2.2 ml) is added to a solution of 1-(3,4-dichlorophenyl)-3,3-bis(methylthio)prop-2-en-1-one (2.0 g) in ethanol (70 ml) and heated to 80° C. over night. Hydrazine-hydrate (1 ml) is added to the reaction mixture and the mixture is stirred over night at 80° C. The solvent is removed under ... | inputs[4]:
- identifiers[1]{type,value}:
NAME,"1,4-dioxa-8-azaspiro[4.5]decane"
reaction_role: REACTANT
amount:
type: volume
value: 2.2
unit: milliliter
- identifiers[1]{type,value}:
NAME,"1-(3,4-dichlorophenyl)-3,3-bis(methylthio)prop-2-en-1-one"
reaction_role: REACTANT
am... |
Extract the chemical reaction information from the given text | 0.62 g of phenylacetyl chloride is added dropwise under ice-cooling to a mixture of 0.35 g of 1-(3-hydroxyphenyl)7-methyl-6-azabicyclo[3,2,1]octane, 1 ml of triethylamine and 7 ml of methylenedichloride. The mixture is stirred at room temperature for 20 hours. Then, the mixture is concentrated under reduced pressure. W... | inputs[8]:
- identifiers[1]{type,value}:
NAME,phenylacetyl chloride
reaction_role: REACTANT
amount:
type: mass
value: 0.62
unit: gram
- identifiers[1]{type,value}:
NAME,lithium aluminium hydride
reaction_role: REACTANT
amount:
type: mass
value: 0.6
unit: g... |
Extract the chemical reaction information from the given text | 4-(5-Methoxy-2-methoxymethylindol-1-yl)phenol (0.43 mmol) was dissolved in N,N-dimethylformamide under N2. 1-(3-Chloropropyl)pyrrolidine (74 mg, 0.5 mmol), sodium hydride (20 mg, 60% wt dispersion in mineral oil, 0.5 mmol) and sodium iodide (75 mg, 0.5 mmol) were added, and the mixture was heated at 70° C. for 2 hours.... | inputs[5]:
- identifiers[1]{type,value}:
NAME,4-(5-Methoxy-2-methoxymethylindol-1-yl)phenol
reaction_role: REACTANT
amount:
type: moles
value: 0.43
unit: millimole
- identifiers[1]{type,value}:
NAME,"N,N-dimethylformamide"
reaction_role: SOLVENT
- identifiers[1]{type,value}:
... |
Extract the chemical reaction information from the given text | To a 1 L 3-neck flask equipped with overhead stirrer was added crude 5-(1-butoxy-vinyl)-4-methyl-3H-isobenzofuran-1-one (55.8 g) and THF (315 mL). The solution was cooled to <5° C. after which water (79 mL) was added and the solution was maintained at <5° C. NBS (41.6 g) was then added portion-wise while maintaining Tm... | inputs[4]:
- identifiers[1]{type,value}:
NAME,HBr
reaction_role: REACTANT
amount:
type: volume
value: 0.241
unit: milliliter
- identifiers[1]{type,value}:
NAME,THF
reaction_role: SOLVENT
- identifiers[1]{type,value}:
NAME,NBS
reaction_role: REACTANT
amount:
... |
Extract the chemical reaction information from the given text | A mixture of (E)-4-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-2-(trifluoromethoxy)benzoic acid (0.25 g, 0.52 mmol), 2-amino-N-(2,2,2-trifluoroethyl)acetamide (0.158 g, 0.62 mmol), PyBOP (0.40 g, 0.78 mmol) and DIPEA (0.134 g, 1.04 mmol) in CH2Cl2 (10.0 mL) were stirred at ambient temperature for 16 h. ... | inputs[5]:
- identifiers[1]{type,value}:
NAME,"(E)-4-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-2-(trifluoromethoxy)benzoic acid"
reaction_role: REACTANT
amount:
type: mass
value: 0.25
unit: gram
- identifiers[1]{type,value}:
NAME,"2-amino-N-(2,2,2-trifluoroethyl)a... |
Extract the chemical reaction information from the given text | Under nitrogen, to (S)-2-(1-aminopropyl)-5-fluoro-3-(4-(2,2,2-trifluoroethoxy)phenyl)quinazolin-4(3H)-one (35 mg, 0.089 mmol, 1.0 equiv) in t-BuOH (0.09 mL) at 23° C. was added 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (16 mg, 0.11 mmol, 1.2 equiv) and diisopropylethylamine (31 μL, 0.18 mmol, 2.0 equiv). After stirring for ... | inputs[4]:
- identifiers[1]{type,value}:
NAME,"(S)-2-(1-aminopropyl)-5-fluoro-3-(4-(2,2,2-trifluoroethoxy)phenyl)quinazolin-4(3H)-one"
reaction_role: REACTANT
amount:
type: mass
value: 35.0
unit: milligram
- identifiers[1]{type,value}:
NAME,"4-chloro-7H-pyrrolo[2,3-d]pyrimidine"
... |
Extract the chemical reaction information from the given text | 3-Amino-4-(2-hydroxy-2-methylpropylamino)quinoline (7.5 g, 32 mmol) was combined with methoxyacetic acid (7.5 mL, 97 mmol) and heated at about 170° C. for about 3 hours. The resulting solid residue was dissolved in ethyl acetate (150 mL). The ethyl acetate solution was extracted twice with 0.2N sodium hydroxide, washed... | inputs[3]:
- identifiers[1]{type,value}:
NAME,3-Amino-4-(2-hydroxy-2-methylpropylamino)quinoline
reaction_role: REACTANT
amount:
type: mass
value: 7.5
unit: gram
- identifiers[1]{type,value}:
NAME,methoxyacetic acid
reaction_role: REACTANT
amount:
type: volume
v... |
Extract the chemical reaction information from the given text | To a stirred suspension of 1.29 g of magnesium and 10 mg of mercuric chloride in 12 ml of ether is added 0.4 ml of propargyl bromide. The reaction is initiated after stirring at room temperature for a few minutes. The stirred mixture is cooled in an ice-water bath and a solution of 9.64 g of n-butyl trimethylsilylethyn... | inputs[5]:
- identifiers[1]{type,value}:
NAME,magnesium
reaction_role: REACTANT
amount:
type: mass
value: 1.29
unit: gram
- identifiers[1]{type,value}:
NAME,mercuric chloride
reaction_role: REACTANT
amount:
type: mass
value: 10.0
unit: milligram
- identi... |
Extract the chemical reaction information from the given text | A mixture of 9-piperidin-4-yl-2-[2-(2,2,2-trifluoro-ethyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-6-oxa-1,10b-diaza-benzo[e]azulene (180 mg, 0.43 mmol) in DMF (1 mL) was treated with potassium carbonate (89 mg, 0.65 mmol) and bromo acetamide (77 mg, 0.56 mmol) and then stirred at RT for 18 h. The reaction mixture was part... | inputs[4]:
- identifiers[1]{type,value}:
NAME,"9-piperidin-4-yl-2-[2-(2,2,2-trifluoro-ethyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-6-oxa-1,10b-diaza-benzo[e]azulene"
reaction_role: REACTANT
amount:
type: mass
value: 180.0
unit: milligram
- identifiers[1]{type,value}:
NAME,DMF
rea... |
Extract the chemical reaction information from the given text | To a solution of (E)-1-(1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone O-2-hydroxyethyl oxime (example 23) (200 mg, 0.55 mmol) in THF (10 mL) were added triphenylphosphine (144 mg, 0.55 mmol), isoindoline-1,3-dione (81 mg, 0.55 mmol) and (E)-diisopropyl diazene-1,2-dicarboxylate (111 mg, 0.55 mm... | inputs[5]:
- identifiers[1]{type,value}:
NAME,"(E)-1-(1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone O-2-hydroxyethyl oxime"
reaction_role: REACTANT
amount:
type: mass
value: 200.0
unit: milligram
- identifiers[1]{type,value}:
NAME,triphenylphosphine
rea... |
Extract the chemical reaction information from the given text | A solution of ((R)-2-Hydroxy-1,2-dimethyl-propyl)-carbamic acid tert-butyl ester (4 g, 19.68 mmol) in CH2Cl2 (100 mL) at −78° C. was added DAST (2.86 mL, 21.65 mmol) dropwise and the resulting mixture was warmed to rt and stirred for 16 hrs. The reaction mixture was quenched with sat. NaHCO3 (100 mL). The organic phase... | inputs[3]:
- identifiers[1]{type,value}:
NAME,"((R)-2-Hydroxy-1,2-dimethyl-propyl)-carbamic acid tert-butyl ester"
reaction_role: REACTANT
amount:
type: mass
value: 4.0
unit: gram
- identifiers[1]{type,value}:
NAME,DAST
reaction_role: REACTANT
amount:
type: volume
... |
Extract the chemical reaction information from the given text | 0.07 ml of trimethylsilyl bromide is added to a solution of 0.1 g of 5-benzyloxy-7-hydroxymethyl-1,4-benzodioxane in 5 ml of chloroform and the mixture is stirred for a further 15 minutes at room temperature and then concentrated by evaporation in a rotary evaporator. The residue is immediately dissolved in a small amo... | inputs[3]:
- identifiers[1]{type,value}:
NAME,trimethylsilyl bromide
reaction_role: REACTANT
amount:
type: volume
value: 0.07
unit: milliliter
- identifiers[1]{type,value}:
NAME,"5-benzyloxy-7-hydroxymethyl-1,4-benzodioxane"
reaction_role: REACTANT
amount:
type: mass
... |
Extract the chemical reaction information from the given text | Into a 500 mL three-neck flask were added 19 g (60 mmol) of 3-bromo-9-phenylcarbazole, 0.34 g (0.60 mmol) of bis(dibenzylideneacetone)palladium(0), 1.6 g (3.0 mmol) of 1,1-bis(diphenylphosphino)ferrocene, and 13 g (0.18 mol) of sodium tert-butoxide, and the atmosphere in the flask was substituted with nitrogen. Then, 1... | inputs[7]:
- identifiers[1]{type,value}:
NAME,toluene
reaction_role: SOLVENT
amount:
type: volume
value: 500.0
unit: milliliter
- identifiers[1]{type,value}:
NAME,xylene
reaction_role: REACTANT
amount:
type: volume
value: 110.0
unit: milliliter
- identif... |
Extract the chemical reaction information from the given text | To a stirred solution of tert-butyl 5-fluoro-2-oxospiro[indoline-3,3′-piperidine]-1′-carboxylate (0.80 g, 2.5 mmol) in toluene (20 mL) was added dropwise a solution of sodium bis(2-methoxyethoxy)aluminium hybrid (Red-Al) in toluene (65% w/w, 1.1 mL, 3.5 mmol) at about 70° C. under N2. The reaction mixture was stirred a... | inputs[3]:
- identifiers[1]{type,value}:
NAME,"tert-butyl 5-fluoro-2-oxospiro[indoline-3,3′-piperidine]-1′-carboxylate"
reaction_role: REACTANT
amount:
type: mass
value: 0.8
unit: gram
- identifiers[1]{type,value}:
NAME,sodium bis(2-methoxyethoxy)aluminium
reaction_role: REACTA... |
Extract the chemical reaction information from the given text | 3-Nitro-pyridine-2-sulfonic acid amide (3 g, 14.77 mmol) and iron powder (5 g, <10 micron) were suspended in ethanol (100 mL). Saturated aqueous ammonium chloride solution (60 mL) was added and the mixture stirred at 105° C. for 1.5 h. Upon cooling to 25° C., ethyl acetate (200 mL) was added and the mixture was shaken ... | inputs[5]:
- identifiers[1]{type,value}:
NAME,ethanol
reaction_role: SOLVENT
amount:
type: volume
value: 100.0
unit: milliliter
- identifiers[1]{type,value}:
NAME,3-Nitro-pyridine-2-sulfonic acid amide
reaction_role: REACTANT
amount:
type: mass
value: 3.0
... |
Extract the chemical reaction information from the given text | 4.76 g (35.3 mmol) of 1-hydroxybenzotriazole and 7.27 g (35.3 mmol) of dicyclohexylcarbodiimide were added to a solution of 7.02 g (29.4 mmol) of 4-(4-methylsulfonylaminophenyl)-4-oxobutyric acid in 60 ml of dimethylformamide at 0° C. and the mixture was stirred at that temperature for 1 h. 4.80 g (35.3 mmol) of 2-(6-m... | inputs[4]:
- identifiers[1]{type,value}:
NAME,1-hydroxybenzotriazole
reaction_role: REACTANT
amount:
type: mass
value: 4.76
unit: gram
- identifiers[1]{type,value}:
NAME,dicyclohexylcarbodiimide
reaction_role: REACTANT
amount:
type: mass
value: 7.27
unit: ... |
Extract the chemical reaction information from the given text | To a solution of methyl 2-(4-fluorophenyl)-3-(1,2,3,4-tetrahydroquinolin-1-yl)quinoxaline-6-carboxylate (300 mg, 0.73 mmol) in chloroform (50 mL) was added sulfuric acid (213.6 mg, 2.18 mmol) and thionyl chloride (514 mg, 4.36 mmol) dropwise with stirring at 85° C. for 3 h in an oil bath. The reaction was then quenched... | inputs[6]:
- identifiers[1]{type,value}:
NAME,ethyl acetate
reaction_role: REACTANT
- identifiers[1]{type,value}:
NAME,petroleum
reaction_role: SOLVENT
- identifiers[1]{type,value}:
NAME,"methyl 2-(4-fluorophenyl)-3-(1,2,3,4-tetrahydroquinolin-1-yl)quinoxaline-6-carboxylate"
reaction_role:... |
Extract the chemical reaction information from the given text | To a solution of 5-(2,3-epoxy-3-methylbutyl)-2-methoxyhydroquinone diacetate (1.848 g) in methanol (36 ml) was added potassium hydrogencarbonate (1.50 g) in one portion. The mixture was stirred for 21 hours at ambient temperature and concentrated in vacuo. The residue was dissolved in a mixture of ethyl acetate (30 ml)... | inputs[3]:
- identifiers[1]{type,value}:
NAME,"5-(2,3-epoxy-3-methylbutyl)-2-methoxyhydroquinone diacetate"
reaction_role: REACTANT
amount:
type: mass
value: 1.848
unit: gram
- identifiers[1]{type,value}:
NAME,potassium hydrogencarbonate
reaction_role: REACTANT
amount:
... |
Extract the chemical reaction information from the given text | {4-[7-((S)-3-tert-Butoxycarbonylamino-pyrrolidine-1-sulfonyl)-1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl]-furazan-3-yl)-carbamic acid tert-butyl ester A solution of the product from Example 279 (0.150 g, 0.367 mmol) in tetrahydrofuran (2 ml) at ambient temperature was treated with NaH (60%) under Argon. After 10 minutes, th... | inputs[7]:
- identifiers[1]{type,value}:
NAME,n-butyllithium
reaction_role: REACTANT
- identifiers[1]{type,value}:
NAME,"{4-[7-((S)-3-tert-Butoxycarbonylamino-pyrrolidine-1-sulfonyl)-1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl]-furazan-3-yl)-carbamic acid tert-butyl ester"
reaction_role: REACTANT
- iden... |
Extract the chemical reaction information from the given text | A 250-mL flask was charged with 2-anilinoethanol (9.17 ml, 73.2 mmol), 9 mL dry EtOH, an overhead stirrer, a calibrated pH probe, and 27 mL water. An addition funnel was charged with 10 N sodium hydroxide solution (45.4 ml, 454 mmol). The solution was heated to 41° C., and treated with chloracetyl chloride (17.5 ml, 22... | inputs[4]:
- identifiers[1]{type,value}:
NAME,chloracetyl chloride
reaction_role: REACTANT
amount:
type: volume
value: 17.5
unit: milliliter
- identifiers[1]{type,value}:
NAME,sodium hydroxide
reaction_role: REACTANT
- identifiers[1]{type,value}:
NAME,2-anilinoethanol
... |
Extract the chemical reaction information from the given text | A mixture of 30 g of p-hydroxyacetophenone and 30 g of potassium carbonate was stirred in 500 ml of ethanol at 60° C. for 30 minutes. After cooling to room temperature, 521 g of ethyl 5-bromo-2,2-dimethylpentanoate was added to the reaction mixture. The resulting mixture was heated under reflux overnight while stirring... | inputs[4]:
- identifiers[1]{type,value}:
NAME,ethanol
reaction_role: SOLVENT
amount:
type: volume
value: 500.0
unit: milliliter
- identifiers[1]{type,value}:
NAME,p-hydroxyacetophenone
reaction_role: REACTANT
amount:
type: mass
value: 30.0
unit: gram
- i... |
Extract the chemical reaction information from the given text | DIEA (0.012 mL, 0.071 mmol) was added to 8-hydroxy-3-carboxy-coumarin (0.013 g, 0.065 mmol) and HATU (0.027 g, 0.071 mmol) in 0.5 mL of DMF with constant stirring at room temperature until a clear solution resulted. Subsequently, 3-(4-oxo-4H-chromen-6-yl)-phenylamine (0.015 g, 0.065 mmol) was added and allowed to react... | inputs[5]:
- identifiers[1]{type,value}:
NAME,3-(4-oxo-4H-chromen-6-yl)-phenylamine
reaction_role: REACTANT
amount:
type: mass
value: 0.015
unit: gram
- identifiers[1]{type,value}:
NAME,DIEA
reaction_role: REACTANT
amount:
type: volume
value: 0.012
unit: m... |
Extract the chemical reaction information from the given text | The operation is carried out as in Stage 1 of Example 10 starting from 280 mg of the product obtained in Stage 1 of Example 7, 3 ml of methylene chloride, 0.17 ml of triethylamine and 280 mg of 4-(trifluoromethyl)benzenesulphonic acid chloride in place of the 4-methyl-benzenesulphonic acid chloride, then the reaction m... | inputs[3]:
- identifiers[1]{type,value}:
NAME,4-(trifluoromethyl)benzenesulphonic acid chloride
reaction_role: REACTANT
amount:
type: mass
value: 280.0
unit: milligram
- identifiers[1]{type,value}:
NAME,methylene chloride
reaction_role: REACTANT
amount:
type: volume
... |
Extract the chemical reaction information from the given text | A heterogeneous mixture of [3-(4-nitrophenyl)-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]acetic acid (31.0 mmol), elemental tin dust (5.30 mmol), 6.0N aqueous hydrochloric acid (5.3 mL) and absolute ethanol (5.3 mL) was stirred at 70° C. for 1 h. The solution was filtered through Celite and concentrated in vacuo... | inputs[5]:
- identifiers[1]{type,value}:
NAME,phenyl isocyanate
reaction_role: REACTANT
amount:
type: moles
value: 11.17
unit: millimole
- identifiers[1]{type,value}:
NAME,"[3-(4-nitrophenyl)-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]acetic acid"
reaction_role: REACTANT... |
Extract the chemical reaction information from the given text | 1-tert-Butoxy-2-(2-nitrovinyl)benzene (685 mg, 3.10 mmol) in tetrahydrofuran (10 ml) was cooled to 0° C. under an argon atmosphere (balloon). Lithium aluminum hydride (1 M in THF) (12384 μL, 12.4 mmol, equivalent to 470 mg) was added dropwise over 5 minutes. The reaction was stirred at 0° C. for 30 minutes and then at ... | inputs[3]:
- identifiers[1]{type,value}:
NAME,1-tert-Butoxy-2-(2-nitrovinyl)benzene
reaction_role: REACTANT
amount:
type: mass
value: 685.0
unit: milligram
- identifiers[1]{type,value}:
NAME,tetrahydrofuran
reaction_role: SOLVENT
amount:
type: volume
value: 10.0... |
Extract the chemical reaction information from the given text | tert-Butyl(2S)-2-((3S)-3-{[(benzyloxy)carbonyl]amino}-2-oxopyrrolidin-1-yl)propanoate (0.5 g) was dissolved in DCM (7 ml), and trifluoroacetic acid (4.7 ml) was added. The mixture was stirred at room temperature for 4 h and then concentrated under reduced pressure to give the title compound (0.423 g) as a colourless oi... | inputs[3]:
- identifiers[1]{type,value}:
NAME,"tert-Butyl(2S)-2-((3S)-3-{[(benzyloxy)carbonyl]amino}-2-oxopyrrolidin-1-yl)propanoate"
reaction_role: REACTANT
amount:
type: mass
value: 0.5
unit: gram
- identifiers[1]{type,value}:
NAME,DCM
reaction_role: SOLVENT
amount:
... |
Extract the chemical reaction information from the given text | A mixture of 405.9 mg of 2,4-dichloro-6-methylpyrimidine, 585.5 mg of 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-amine (WO2006/046734, page 132, Reference 2), 231.9 mg of 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, 208.6 mg of tris(dibenzylideneacetone)dipalladium(0)-chloroform complex, 751.2 mg of potassiu... | inputs[6]:
- identifiers[1]{type,value}:
NAME,"2,4-dichloro-6-methylpyrimidine"
reaction_role: REACTANT
amount:
type: mass
value: 405.9
unit: milligram
- identifiers[1]{type,value}:
NAME,1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-amine
reaction_role: REACTANT
amount:... |
Extract the chemical reaction information from the given text | 3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylic acid (0.82 g, 3.40 mmol) is stirred together with 0.34 g (3.40 mmol) potassium bicarbonate in 10 ml THF/DMF (1:1) for 15 minutes. Then 1.0 g (3.40 mmol) α-cyano-4-fluoro-3-phenoxybenzyl methanesulfonate in 5 ml THF/DMF (1:1) is added and the mixture stirred for app... | inputs[4]:
- identifiers[1]{type,value}:
NAME,α-cyano-4-fluoro-3-phenoxybenzyl methanesulfonate
reaction_role: REACTANT
amount:
type: mass
value: 1.0
unit: gram
- identifiers[1]{type,value}:
NAME,"3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylic acid"
reaction_role: REACT... |
Extract the chemical reaction information from the given text | A solution of phenyl-[1-(2-phenylethyl)-4-piperidyl]-ketone (0.10 g) in tetrahydrofuran (0.40 g) was added to wet surface-modified adsorbent of Example 10 (1.0 g) in excess aqueous NaOH pH 9.0 (2.0 mL). This mixture was stirred at ambient temperature for 30 minutes. After this, NaBH4 (20 mg) was added and the resulting... | inputs[5]:
- identifiers[1]{type,value}:
NAME,tetrahydrofuran
reaction_role: SOLVENT
amount:
type: mass
value: 0.4
unit: gram
- identifiers[1]{type,value}:
NAME,"phenyl-[1-(2-phenylethyl)-4-piperidyl]-ketone"
reaction_role: REACTANT
amount:
type: mass
value: 0.1... |
Extract the chemical reaction information from the given text | A mixture of 1-cyano-1-(2,4-dimethylphenyl)propan-2-one (43.8 g, 0.23 mol), hydrazine-hydrate (22 mL, 0.46 mol), glacial acetic acid (45 mL, 0.78 mol) and toluene (500 mL) were stirred at reflux temperature for 18 hours in an apparatus fitted with a Dean-Stark trap. The reaction mixture was cooled to ambient temperatur... | inputs[4]:
- identifiers[1]{type,value}:
NAME,"1-cyano-1-(2,4-dimethylphenyl)propan-2-one"
reaction_role: REACTANT
amount:
type: mass
value: 43.8
unit: gram
- identifiers[1]{type,value}:
NAME,hydrazine-hydrate
reaction_role: REACTANT
amount:
type: volume
value: ... |
Extract the chemical reaction information from the given text | To a stirring, degassed mixture of 7-bromo-8-iodo-2-isobutyl-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (0.1 g, 0.25 mmol), 4-methylphenylboronic acid (0.04 g, 0.28 mmol), and tetrakis(triphenylphosphine)palladium (15 mg, 0.013 mmol) in dioxane (2.0 mL) at 20° C. was added K2CO3 (0.04 g, 0.28 mmol) in water (0.6 mL). The ... | inputs[5]:
- identifiers[1]{type,value}:
NAME,K2CO3
reaction_role: REACTANT
amount:
type: mass
value: 0.04
unit: gram
- identifiers[1]{type,value}:
NAME,"7-bromo-8-iodo-2-isobutyl-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one"
reaction_role: REACTANT
amount:
type: mass
... |
Extract the chemical reaction information from the given text | Ethyl 3-{4-[2-(4-Chlorobenzenesulfonamido)-2-(3-pyridyl)ethyl]phenyl}propionate (49 mg) was dissolved in a mixed solvent of 1 ml of ethanol and 1 ml of tetrahydrofuran, followed by addition of 0.30 ml of aqueous 2N sodium hydroxide solution, and stirred at 60° C. for 20 minutes. The reaction mixture was concentrated un... | inputs[4]:
- identifiers[1]{type,value}:
NAME,"Ethyl 3-{4-[2-(4-Chlorobenzenesulfonamido)-2-(3-pyridyl)ethyl]phenyl}propionate"
reaction_role: REACTANT
amount:
type: mass
value: 49.0
unit: milligram
- identifiers[1]{type,value}:
NAME,ethanol
reaction_role: SOLVENT
amount:
... |
Extract the chemical reaction information from the given text | In 2 ml of N,N-dimethylformamide were dissolved 153 mg of 4-(2-butynyloxy)-6-(ethylamino)pyrimidine and 67 mg of allyl chloride, to which 40 mg of sodium hydride (60% in oil) was added, followed by stirring at room temperature for 3 hours. Then, ice water was added to the reaction mixture, which was extracted with ethy... | inputs[5]:
- identifiers[1]{type,value}:
NAME,ice water
reaction_role: REACTANT
- identifiers[1]{type,value}:
NAME,4-(2-butynyloxy)-6-(ethylamino)pyrimidine
reaction_role: REACTANT
amount:
type: mass
value: 153.0
unit: milligram
- identifiers[1]{type,value}:
NAME,allyl ch... |
Extract the chemical reaction information from the given text | A small screw cap test tube was charged with Thiophene-2-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (as prepared in Example 45, 100 mg, 0.256 mmol) and THF (2 mL). To the resulting solution was added 5-amino-2-methoxyphenol (43 mg, 0.309 mmol), and the mixture was stirr... | inputs[3]:
- identifiers[1]{type,value}:
NAME,"Thiophene-2-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide"
reaction_role: REACTANT
amount:
type: mass
value: 100.0
unit: milligram
- identifiers[1]{type,value}:
NAME,THF
reaction_role:... |
Extract the chemical reaction information from the given text | 100 mg (0.51 mmol) of N-cyclopropyl-N-piperidin-4-ylpropionamide, 170 mg (0.51 mmol) of 2-{3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxyphenyl)propanoic acid (cf. preparation 2-3), 108 mg (0.56 mmol) of EDC and 76 mg (0.56 mmol) of HOBT are dissolved in 5 mL of DMF under nitrogen. The mixture is stirred at room tem... | inputs[5]:
- identifiers[1]{type,value}:
NAME,N-cyclopropyl-N-piperidin-4-ylpropionamide
reaction_role: REACTANT
amount:
type: mass
value: 100.0
unit: milligram
- identifiers[1]{type,value}:
NAME,"2-{3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxyphenyl)propanoic acid"
reacti... |
Extract the chemical reaction information from the given text | To a nitrogen-saturated suspension of N-triphenylmethyl-5-[4′-methylbiphenyl-2-yl]tetrazole (10 g, 20.9 mmol) in DCM was added NBS (3.7 g, 20.9 mmol) and a catalytic amount of benzoyl peroxide (60 mg, 0.24 mmol). The mixture was stirred at reflux for 15 hours. After cooling to room temperature, the precipitate was filt... | inputs[4]:
- identifiers[1]{type,value}:
NAME,"N-triphenylmethyl-5-[4′-methylbiphenyl-2-yl]tetrazole"
reaction_role: REACTANT
amount:
type: mass
value: 10.0
unit: gram
- identifiers[1]{type,value}:
NAME,DCM
reaction_role: SOLVENT
- identifiers[1]{type,value}:
NAME,NBS
... |
Extract the chemical reaction information from the given text | A 250 ml, three-necked flask was fitted with a large magnetic, egg-shaped stir bar, a thermocouple, reflux condenser, and an argon inlet. This apparatus was dried in an oven overnight at 125° C., assembled hot, and allowed to cool to room temperature in a stream of argon. The flask was charged with 15.09 grams (0.100 m... | inputs[5]:
- identifiers[1]{type,value}:
NAME,Imidazole
reaction_role: REACTANT
- identifiers[1]{type,value}:
NAME,silyl chloride
reaction_role: REACTANT
- identifiers[1]{type,value}:
NAME,t-butyldimethylsilyl chloride
reaction_role: REACTANT
amount:
type: mass
value: 15.09... |
Extract the chemical reaction information from the given text | Diacetoxycopper (907 mg) was added to a mixture of pyridine (0.606 mL), 2-chloro-5-(trifluoromethyl)phenylboronic acid (459 mg), 4-[(9S)-2,2-dioxido-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazin-9-yl]phenol (700 mg) and cesium carbonate (814 mg) in MeCN (25 mL). The mixture was stirred at room temperature under a... | inputs[6]:
- identifiers[1]{type,value}:
NAME,pyridine
reaction_role: REACTANT
amount:
type: volume
value: 0.606
unit: milliliter
- identifiers[1]{type,value}:
NAME,2-chloro-5-(trifluoromethyl)phenylboronic acid
reaction_role: REACTANT
amount:
type: mass
value: ... |
End of preview. Expand in Data Studio
README.md exists but content is empty.
- Downloads last month
- 13