Triethylamine → N-(4-bromo-1-methyl-1H-pyrazol-3-yl)-4-chlorobutanamide
Reaction equation
[Br:1][C:2]1[C:3]([NH2:8])=[N:4][N:5]([CH3:7])[CH:6]=1.C(N(CC)CC)C.[Cl:16][CH2:17][CH2:18][CH2:19][C:20](Cl)=[O:21].[Cl-].[NH4+]>C1COCC1>[Br:1][C:2]1[C:3]([NH:8][C:20](=[O:21])[CH2:19][CH2:18][CH2:17][Cl:16])=[N:4][N:5]([CH3:7])[CH:6]=1Participants
6
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 4-bromo-1-methyl-1H-pyrazol-3-amine (310 mg) and triethylamine (0.37 mL) in THF (8.8 mL) was added 4-chlorobutanoyl chloride (0.22 mL) under ice-cooling, and the mixture was stirred at 0° C. for 30 min. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (456 mg).
Workup
- temperaturecooling
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-1d3631e8debd4ebaa2d974ef803fcf94
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321757B2
Reaction notes
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