[CH:1]1([CH2:7][NH:8][C:9]([NH:11][NH:12][C:13](=O)[CH2:14][CH:15]([N:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[O:29][CH3:30])[CH2:19][CH2:18]2)[CH3:16])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>[OH-].[Na+]>[CH:1]1([CH2:7][N:8]2[C:13]([CH2:14][CH:15]([N:17]3[CH2:22][CH2:21][N:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[O:29][CH3:30])[CH2:19][CH2:18]3)[CH3:16])=[N:12][NH:11][C:9]2=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1N-(Cyclohexylmethyl)-2-{3-[4-(2-methoxyphenyl)piperazin-1-yl]butanoyl}hydrazinecarboxamide D13 (0.90 g, 2.08 mmol) in 2M NaOH aqueous solution (20 mL) was heated at reflux for 18 hrs. The pH was adjusted to 8 with conc. HCl and the resulting yellow slurry was extracted twice with DCM (50 mL and 20 mL). The combined organic extracts were filtered and DCM evaporated under reduced pressure to a light yellow glassy solid. Purification by flash chromatography (Silica gel 60 Å, 45 μm 10% methanol in dichloromethane) afforded 0.42 g (48.8%) 4-(cyclohexylmethyl)-5-{2-[4-(2-methoxyphenyl)piperazin-1-yl]propyl}-2,4-dihydro-3H-1,2,4-triazol-3-one D14 as a cream solid.
Wird geladen…