Cyclopentylamine → 5,6-Dichloro-1-(5-deoxy-beta-D-ribofuranosyl)-N-(cyclopentyl)-1H-benzimidazol-2-amine

HRID 2227212Notes

Reaction equation

HRID 2227212 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]=1

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 5129192-Bromo-5,6-dichloro-1-(5-deoxy-beta-D-ribofuranosyl)-1H-benzimidazole

Product 1

HCID 539927675,6-Dichloro-1-(5-deoxy-beta-D-ribofuranosyl)-N-(cyclopentyl)-1H-benzimidazol-2-amineYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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).

Workup

  1. customreacted for 92 h
  2. customPurification on a silica gel column with 1:15 methanol

Sources & evidence

ORD record
ord-5bc4d0ca3e8c437f90c482e31c0c713f
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

Loading…