Cyclopentylamine → 5,6-Dichloro-1-(5-deoxy-beta-D-ribofuranosyl)-N-(cyclopentyl)-1H-benzimidazol-2-amine
反応式
[CH:1]1([NH2:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:8]1[N:12]([C@@H:13]2[O:19][C@H:18]([CH3:20])[C@@H:16]([OH:17])[C@H:14]2[OH:15])[C:11]2[CH:21]=[C:22]([Cl:26])[C:23]([Cl:25])=[CH:24][C:10]=2[N:9]=1>C(Cl)Cl>[Cl:25][C:23]1[C:22]([Cl:26])=[CH:21][C:11]2[N:12]([C@@H:13]3[O:19][C@H:18]([CH3:20])[C@@H:16]([OH:17])[C@H:14]3[OH:15])[C:8]([NH:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[N:9][C:10]=2[CH:24]=1参加物
4
実験手順
Following General Procedure V, cyclopentyl amine (Aldrich, 5 mL, 50.68 mmol), and 2-bromo-5,6-dichloro-1-(5-deoxy-beta-D-ribofuranosyl)-1H-benzimidazole (250 mg, 0.65 mmol) reacted for 92 h. Purification on a silica gel column with 1:15 methanol:CH2Cl2 gave the title compound (238 mg, 0.62 mmol, 95%); MS (EI): m/z (rel. intensity) 386 (0.20, M+); 1H NMR (DMSO-d6) δ7.42 (s, 1H, Ar—H), 7.33 (s, 1H, Ar—H), 6.68 (d, 1H, NH, J=6.7 Hz), 5.71 (d, 1H, CH, J=6.8 Hz), 5.29 (m, 2H, overlapping OH), 4.32 (m, 1H. CH), 4.16 (m, 1H, CH), 3.92 (m, 1H, CH), 3.81 (m, 1H, CH), 1.95 (m, 2H, CH2), 1.70 (m, 2H, CH2), 1.56 (m, 4H, CH2), 1.38 (d, 3H, CH3, J=6.4 Hz).