Methyl isothiocyanate → 4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-N-methyl-[1,3'-bipiperidine]-1'-carbothioamide
반응식
[N:1]([CH3:4])=[C:2]=[S:3].[N:5]1([CH:29]2[CH2:34][CH2:33][CH2:32][NH:31][CH2:30]2)[CH2:10][CH2:9][CH:8]([NH:11][C:12]2[N:16]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[C:15]3[CH:25]=[CH:26][CH:27]=[CH:28][C:14]=3[N:13]=2)[CH2:7][CH2:6]1>O1CCCC1>[F:24][C:21]1[CH:20]=[CH:19][C:18]([CH2:17][N:16]2[C:15]3[CH:25]=[CH:26][CH:27]=[CH:28][C:14]=3[N:13]=[C:12]2[NH:11][CH:8]2[CH2:7][CH2:6][N:5]([CH:29]3[CH2:34][CH2:33][CH2:32][N:31]([C:2](=[S:3])[NH:1][CH3:4])[CH2:30]3)[CH2:10][CH2:9]2)=[CH:23][CH:22]=1참가 물질
4
실험 절차
A mixture of 0.8 parts of isothiocyanatomethane, 4 parts of N-([1,3'-bipiperidin]-4-yl)-1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-amine and 90 parts of tetrahydrofuran was stirred overnight at room temperature. The reaction mixture was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (96:4 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile, yielding 3.7 parts (77%) of 4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-N-methyl-[1,3'-bipiperidine]-1'-carbothioamide; mp. 218.8° C. (compound 37).