[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][C:20]([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)=[O:21])[CH2:15][CH2:14]3)[S:10][N:9]=2)=[CH:4][CH:3]=1.[BH4-].[Na+].O.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]=[C:11]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH:20]([C:22]4[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=4)[OH:21])[CH2:15][CH2:14]3)[S:10][N:9]=2)=[CH:6][CH:7]=1A mixture of 2-(4-(3-(4-chlorophenyl)-1,2,4-thiadiazol-5-yl)piperazin-1-yl)-1-(4-methoxyphenyl)ethanone (75 mg, 175 μmol) and NaBH4 (10 mg, 264 μmol) in THF (5 mL) and MeOH (1 mL) was stirred at RT. Water (5 mL) and 10% aq.Na2CO3 (5 mL) was added and stirred for 10 min. The mixture was extracted with EtOAc; the organic layers were washed with brine (20 mL), dried over Na2SO4, filtered off and concentrated in vacuo.
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