HCID 10274305、化合物 → 1-[(2S,3R)-2-hydroxy-5-(6-quinolyloxy)-3-pentyl]imidazole-4-carboxamide

反応式

C([O:8][C@H:9]([C@H:11]([N:25]1[CH:29]=[C:28]([C:30]([NH2:32])=[O:31])[N:27]=[CH:26]1)[CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)[CH3:10])C1C=CC=CC=1>C1CCCCC=1.C(O)C.[OH-].[OH-].[Pd+2]>[OH:8][C@H:9]([C@H:11]([N:25]1[CH:29]=[C:28]([C:30]([NH2:32])=[O:31])[N:27]=[CH:26]1)[CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)[CH3:10]

参加物

実験手順

To a solution of 1-[(2S,3R)-2-benzyloxy-5-(6-quinolyloxy)-3-pentyl]imidazole-4-carboxamide (58 mg, 0.135 mmol) in cyclohexene (2.5 ml) and ethanol (5 ml) was added 20% palladium hydroxide on carbon (50 mg). The resulting mixture was stirred at reflux for 8 h. After cooling to room temperature, the mixture was filtered through Celite and washed with ethanol. The filtrate was concentrated in vacuo and then the residue was purified by silica gel (1.5 g) chromatography eluted with chloroform/methanol (50:1 to 10:1) to give 1-[(2S,3R)-2-hydroxy-5-(6-quinolyloxy)-3-pentyl]imidazole-4-carboxamide (2) (39.8 mg, 86.8%).