[Cl:1][C:2]1[CH:3]=[C:4]([C:27](=[O:29])[CH3:28])[CH:5]=[N:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14]2[NH:18][C:17]3[CH:19]=[C:20]([C:23]([F:26])([F:25])[F:24])[CH:21]=[CH:22][C:16]=3[N:15]=2)[CH2:10][CH2:9]1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]([OH:29])[CH3:28])[CH:5]=[N:6][C:7]=1[N:8]1[CH2:9][CH2:10][N:11]([C:14]2[NH:18][C:17]3[CH:19]=[C:20]([C:23]([F:25])([F:26])[F:24])[CH:21]=[CH:22][C:16]=3[N:15]=2)[CH2:12][CH2:13]1To a solution of 1-{5-chloro-6-[4-(6-trifluoromethyl-1H-benzoimidazol-2-yl)-piperazin-1-yl]-pyridin-3-yl}-ethanone (0.3 g, 0.71 mmol, Example 97e) in MeOH (20 mL) was added portionwise NaBH4 (0.037 g, 1.0 mmol, Aldrich) with stirring at 0° C. The reaction mixture was stirred at 0° C. for 30 min, quenched with 20 mL of satd. aq. NaHCO3, and diluted with EtOAc (50 mL). The organic phase was separated, washed with brine (20 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was recrystallized from 1:1 EtOAc/hexane mixture to give the title compound as a white foam. MS (ESI, pos. ion) m/z: 426 (M+1).
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