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

HRID 2227213Notes

Reaction equation

HRID 2227213 reaction equation
[CH2:1]([NH2:4])[CH:2]=[CH2:3].Br[C:6]1[N:10]([C@@H:11]2[O:17][C@H:16]([CH3:18])[C@@H:14]([OH:15])[C@H:12]2[OH:13])[C:9]2[CH:19]=[C:20]([Cl:24])[C:21]([Cl:23])=[CH:22][C:8]=2[N:7]=1>C(Cl)Cl>[Cl:23][C:21]1[C:20]([Cl:24])=[CH:19][C:9]2[N:10]([C@@H:11]3[O:17][C@H:16]([CH3:18])[C@@H:14]([OH:15])[C@H:12]3[OH:13])[C:6]([NH:4][CH2:1][CH:2]=[CH2:3])=[N:7][C:8]=2[CH:22]=1

Participants

4

Reactant 2

HCID 7853AllylamineHCID 5129192-Bromo-5,6-dichloro-1-(5-deoxy-beta-D-ribofuranosyl)-1H-benzimidazole

Product 1

HCID 539918385,6-Dichloro-1-(5-deoxy-beta-D-ribofuranosyl)-N-(2-propenyl)-1H-benzimidazol-2-amineYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following General Procedure V, allylamine (Aldrich, 5 mL, 66.64 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 1:25 methanol:CH2Cl2 gave the title compound (195 mg, 0.54 mmol, 84%); MS (EI): m/z (rel. intensity) 358 (0.05, M+); 1H NMR (DMSO-d6) δ7.41 (s, 1H, Ar—H), 7.36 (s, 1H, Ar—H), 7.10 (t, 1H, NH, J=11.2 Hz), 5.94 (m, 1H, CH), 5.70 (d, 1H, CH, J=6.5 Hz), 5.25 (m, 3H, overlapping OH and CH2), 5.09 (d, 1H, OH, J=8.8 Hz), 4.35 (m, 1H, CH), 3.98 (m, 2H, CH2), 3.92 (m, 1H, CH), 3.81 (m, 1H, CH), 1.38 (d, 3H, CH3, J=6.5 Hz).

Workup

  1. customreacted for 92 h
  2. customPurification on a silica gel column with 1:25 methanol

Sources & evidence

ORD record
ord-02bd44ab4c5545c7a97fdeb30da641aa
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

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