[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[C:6]([C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=O)=[O:7].[Cl:22][C:23]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[C:25]([Cl:33])[C:24]=1[NH:34][NH2:35].O>C1(C)C=CC=CC=1>[Cl:22][C:23]1[CH:28]=[C:27]([C:29]([F:31])([F:30])[F:32])[CH:26]=[C:25]([Cl:33])[C:24]=1[NH:34][N:35]=[C:10]([OH:12])[C:9]1[CH:13]=[CH:14][CH:15]=[N:16][C:8]=1[C:6](=[O:7])[C:5]1[CH:17]=[CH:18][CH:19]=[C:3]([C:2]([F:1])([F:21])[F:20])[CH:4]=1A suspension of 2-(3-trifluoromethylbenzoyl)nicotinic acid (1.5 g) and 2,6-dichloro-4-trifluoromethylphenylhydrazine (1.87 g) in toluene was stirred at reflux with azeotropic removal of water (using a Dean Stark apparatus) for 6.5 hours. The mixture was cooled to room temperature and then washed with 2N hydrochloric acid and water. The organic phase was dried and evaporated. The crude product was purified by column chromatography to yield a yellow gum which was triturated in hexane to yield the title compound as a pale yellow solid (0.24 g), m.p. 92°-96° C.
불러오는 중…