Cyclohexene oxide → N-(6-{4-[4-((1S,2S)-2-hydroxy-cyclohexyl)piperazine-1-carbonyl]phenoxy}pyridin-3-yl)-4-trifluoromethylbenzamide
Reaction equation
[N:1]1([C:7]([C:9]2[CH:34]=[CH:33][C:12]([O:13][C:14]3[N:19]=[CH:18][C:17]([NH:20][C:21](=[O:32])[C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=4)=[CH:16][CH:15]=3)=[CH:11][CH:10]=2)=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[O:35]1[CH:37]2[CH2:38][CH2:39][CH2:40][CH2:41][CH:36]12>CO>[OH:35][C@H:36]1[CH2:41][CH2:40][CH2:39][CH2:38][C@@H:37]1[N:4]1[CH2:5][CH2:6][N:1]([C:7]([C:9]2[CH:10]=[CH:11][C:12]([O:13][C:14]3[N:19]=[CH:18][C:17]([NH:20][C:21](=[O:32])[C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:24][CH:23]=4)=[CH:16][CH:15]=3)=[CH:33][CH:34]=2)=[O:8])[CH2:2][CH2:3]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of N-{6-[4-(piperazine-1-carbonyl)phenoxy]-pyridin-3-yl}-4-trifluoromethyl-benzamide (430 mg, 0.91 mmol) in methanol was added 1,2-epoxycyclohexane (180 mg, 1.83 mmol), and the resulting solution was stirred for 1 day under reflux. The resulting reaction solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=35:1), and then ethyl acetate was added. The precipitated white powder was filtered off and washed with ethyl acetate, to thereby yield 284 mg of the title compound.