Methanol → HCID 178463675, compound

Reaction equation

[F:1][C:2]([F:26])([F:25])[C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]([CH:14]3[CH2:19][CH2:18][CH:17]([CH2:20][NH:21][C:22](=O)[CH3:23])[CH2:16][CH2:15]3)[NH:12][CH:13]=2)[CH:6]=[CH:7][CH:8]=1.CSC.B.CO>C1COCC1>[CH2:22]([NH:21][CH2:20][CH:17]1[CH2:16][CH2:15][CH:14]([C:11]2[NH:12][CH:13]=[C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:25])([F:26])[F:1])[CH:4]=3)[N:10]=2)[CH2:19][CH2:18]1)[CH3:23]

Participants

Procedure

To a solution of (N-{4-[4-(3-Trifluoromethyl-phenyl)-1H-imidazol-2-yl]-cyclohexylmethyl}-acetamide (207 mg, 0.57 mmol, from Example 2A) in THF, 3 equivalents of borane dimethylsulfide (2M in THF) was added, and the solution stirred overnight at room temperature. One volume of MeOH was added to the reaction mixture, and the mixture was concentrated under reduced pressure. 50 mL of 3N HCl was added, and the mixture was warmed for 5 minutes. After washing the solution with ether, the solution was made basic with NaOH and extracted with ethyl acetate. The solution was dried (Na2SO4), concentrated under reduced pressure, and purified using preparative plate chromatography to give Ethyl-{4-[4-(3-trifluoromethyl-phenyl)-1H-imidazole-2-yl]cyclohexylmethyl}-amine.