Dimethylformamide → HCID 11524105, compound
Reaction equation
C(Cl)(=O)C(Cl)=O.CN(C)C=O.[F:12][CH:13]([F:23])[C:14]1[C:18]([C:19](O)=[O:20])=[CH:17][N:16]([CH3:22])[N:15]=1.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=2[NH2:38])=[CH:27][C:26]=1[F:39]>ClCCl.O>[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=2[NH:38][C:19]([C:18]2[C:14]([CH:13]([F:23])[F:12])=[N:15][N:16]([CH3:22])[CH:17]=2)=[O:20])=[CH:27][C:26]=1[F:39]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
1.6 ml (18.4 mmol) of oxalyl dichloride and 0.2 ml of dimethylformamide are added to a mixture consisting of 2.96 g (16.8 mmol) of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid in 100 ml of dichloromethane. After 2 hours at room temperature, a solution consisting of 3.83 g (16.0 mmol) of 4′-chloro-5,3′-difluorobiphenyl-2-yl-amine and 2.9 ml (20.8 mmol) in 100 ml of dichloromethane is added. The reaction mixture is stirred for 16 hours at room temperature. For work-up, the reaction mixture is poured into water, and the organic phase is separated, dried over magnesium sulphate and concentrated in vacuo. Column chromatography (petroleum ether/acetone 3:1) yields 5.94 g (93% of theory) of N-(4′-chloro-3′,5-difluorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide with a logP (pH 2.3) of 3.05.
Workup
- additionis added
- customthe organic phase is separated
- dry with materialdried over magnesium sulphate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-84d45c346488416aaf44f203542eb4c4
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08580971B2
Reaction notes
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