Ammonium Chloride → 2-(2-(4-Formyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetamido)-N-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide
Reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[C:7]([CH:8]=[O:9])=[CH:6][NH:5][N:4]=1.CC(C)([O-])C.[K+].Br[CH2:19][C:20]([NH:22][C:23]1[S:27][C:26]2[CH2:28][CH2:29][CH2:30][CH2:31][C:25]=2[C:24]=1[C:32]([NH:34][CH3:35])=[O:33])=[O:21].[NH4+].[Cl-]>C1COCC1>[CH:8]([C:7]1[C:3]([C:2]([F:1])([F:10])[F:11])=[N:4][N:5]([CH2:19][C:20]([NH:22][C:23]2[S:27][C:26]3[CH2:28][CH2:29][CH2:30][CH2:31][C:25]=3[C:24]=2[C:32]([NH:34][CH3:35])=[O:33])=[O:21])[CH:6]=1)=[O:9]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
3-(Trifluoromethyl)pyrazole-4-carbaldehyde (332 mg, 2.02 mmol) was dissolved in THF (10 mL). Potassium tert-butoxide (454 mg, 4.05 mmol) was added, followed by 2-(2-bromoacetamido)-N-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (670 mg, 2.02 mmol). The reaction mixture was stirred at RT overnight. Aqueous NH4Cl (10 mL) was added and the reaction mixture extracted with DCM (3×10 mL). The combined DCM layers were washed with sodium bicarbonate solution (5×10 mL). The aqueous was separated using hydrophobic filter paper and the solvent removed in vacuo to give the desired product as a brown foam (0.73 g, 1.76 mmol, 87%).
Workup
- extractionthe reaction mixture extracted with DCM (3×10 mL)
- washThe combined DCM layers were washed with sodium bicarbonate solution (5×10 mL)
- customThe aqueous was separated
- customthe solvent removed in vacuo
Sources & evidence
- ORD record
- ord-fdbef4c9d84044e89c49d31743ca599d
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07820707B2
Reaction notes
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