Dimethylformamide → N-[1-(Cyanomethyl-carbamoyl)-cyclohexyl]-4-(4-ethyl-piperazin-1-yl)-benzamide

반응식

[C:1]([CH2:3][NH:4][C:5]([C:7]1([NH2:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6])#[N:2].[CH:14]1[CH:15]=[CH:16][C:17]2[N:22](O)N=N[C:18]=2[CH:19]=1.[CH2:24]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[CH3:25].CN([CH:34]=[O:35])C>>[C:1]([CH2:3][NH:4][C:5]([C:7]1([NH:13][C:34](=[O:35])[C:14]2[CH:19]=[CH:18][C:17]([N:22]3[CH2:28][CH2:27][N:26]([CH2:29][CH3:30])[CH2:24][CH2:25]3)=[CH:16][CH:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6])#[N:2]

참가 물질

반응물 4

HCID 6228Dimethylformamide

HCID 8471Triethylamine

HCID 757711-Hydroxybenzotriazole

HCID 111946841-Amino-cyclohexanecarboxylic acid cyanomethyl amide

생성물 1

HCID 10200838N-[1-(Cyanomethyl-carbamoyl)-cyclohexyl]-4-(4-ethyl-piperazin-1-yl)-benzamide

실험 절차

1-Amino-cyclohexanecarboxylic acid cyanomethyl-amide (0.9 mmol) 4-(4-ethyl-piperazin-1-yl)-benzoic acid hydrochloride (0.9 mmol), HOBT (0.9 mmol), WSCD (0.9 mmol) and triethylamine (0.9 mmol) are dissolved in DMF (5 ml) and stirred overnight at rt. After evaporation of the solvent, the residue is dissolved in a mixture of water and sodium carbonate (to ensure slightly basic conditions) and extracted three times with ethyl acetate. The combined extract is dried over sodium sulfate and evaporated. The residue is purified by flash chromatography on silica gel with CH2Cl2/MeOH (with 3N NH3)=93:7 as mobile phase. The product containing fractions are combined and evaporated. The residue is suspended in diethylether and the solid filtered of and dried (vacuum). A white powder is obtained.