4-Cyanobenzoyl chloride → HCID 24759617, 화합물

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[NH2:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[N:29]([CH3:31])[CH3:30])[C:5]([NH:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([C:15]([F:24])([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])=[CH:10][C:9]=1[CH3:25])=[O:6].C(=O)(O)[O-].[Na+].[C:37]([C:39]1[CH:47]=[CH:46][C:42]([C:43](Cl)=[O:44])=[CH:41][CH:40]=1)#[N:38]>C(OCC)(=O)C>[C:37]([C:39]1[CH:47]=[CH:46][C:42]([C:43]([NH:1][C:2]2[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=2[N:29]([CH3:31])[CH3:30])[C:5]([NH:7][C:8]2[C:13]([CH3:14])=[CH:12][C:11]([C:15]([F:24])([C:20]([F:21])([F:22])[F:23])[C:16]([F:18])([F:19])[F:17])=[CH:10][C:9]=2[CH3:25])=[O:6])=[O:44])=[CH:41][CH:40]=1)#[N:38]

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실험 절차

3-Amino-4-dimethylamino-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide (200 mg, 0.44 mmol) (see Example I9) was dissolved in a biphasic mixture of ethyl acetate (4 ml) and aqueous sodium bicarbonate (1N) (4 ml). 4-Cyano-benzoyl chloride (75 mg, 0.44 mmol) was added under vigorous stirring. The reaction mixture was stirred for 18 hours at ambient temperature. The phases were separated, the organic phase was dried over sodium sulfate and concentrated. Purification by chromatography over silica gel (eluent:cyclohexane/ethyl acetate ratio 1:1) gave Compound No. A16 of Table A below (244 mg, 95% yield).