Cyclopentylamine → 5,6-Dichloro-1-(5-deoxy-beta-D-ribofuranosyl)-N-(cyclopentyl)-1H-benzimidazol-2-amine
Reaction equation
[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]=1Participants
4
Procedure
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).