2-Bromo-5,6-dichloro-1-(5-deoxy-beta-D-ribofuranosyl)-1H-benzimidazole → 5,6-Dichloro-1-(5-deoxy-beta-D-ribofuranosyl)-N-((R)-sec-butyl)-1H-benzimidazol-2-amine

HRID 2227214Notes

Reaction equation

HRID 2227214 reaction equation
[C@H:1]([NH2:5])([CH2:3][CH3:4])[CH3:2].Br[C:7]1[N:11]([C@@H:12]2[O:18][C@H:17]([CH3:19])[C@@H:15]([OH:16])[C@H:13]2[OH:14])[C:10]2[CH:20]=[C:21]([Cl:25])[C:22]([Cl:24])=[CH:23][C:9]=2[N:8]=1>>[Cl:24][C:22]1[C:21]([Cl:25])=[CH:20][C:10]2[N:11]([C@@H:12]3[O:18][C@H:17]([CH3:19])[C@@H:15]([OH:16])[C@H:13]3[OH:14])[C:7]([NH:5][C@@H:1]([CH2:3][CH3:4])[CH3:2])=[N:8][C:9]=2[CH:23]=1

Participants

3

Reactant 2

HCID 5129192-Bromo-5,6-dichloro-1-(5-deoxy-beta-D-ribofuranosyl)-1H-benzimidazoleHCID 2724537(R)-sec-butylamine2×

Product 1

HCID 220862695,6-Dichloro-1-(5-deoxy-beta-D-ribofuranosyl)-N-((R)-sec-butyl)-1H-benzimidazol-2-amineYield 53.8%

Conditions

Temperature
80 °C

Procedure

Following General Procedure V, (R)-sec-butylamine (Aldrich, 1.39 mL, 13.70 mmol), and 2-bromo-5,6-dichloro-1-(5-deoxy-beta-D-ribofuranosyl)-1H-benzimidazole (250 mg, 0.65 mmol) were reacted for 65 h. Additional (R)-sec-butylamine (1.39 mL, 13.70 mmol) was added, and the reaction continued to stir at 80° C. for 24 h. Purification on a silica gel column with 1:1 ethyl acetate:hexanes gave the title compound (130 mg, 0.35 mmol, 53%); MS (EI): m/z (rel. intensity) 374 (0.13, M+); 1H NMR (DMSO-d6) δ7.39 (s, 1H, Ar—H), 7.32 (s, 1H, Ar—H), 6.59 (d, 1H, NH, J=7.8 Hz), 5.72 (d, 1H, CH, J=6.6 Hz), 5.26 (m, 2H, overlapping OH), 4.27 (m, 1H, CH), 4.04-3.78 (m, 3H, overlapping CH), 1.61-1.51 (m, 2H, CH2), 1.38 (d, 3H, CH3, J=6.5 Hz), 1.17 (d, 3H, CH3, J=6.5 Hz), 0.89 (t, 3H, CH3, J=14.9 Hz).

Workup

  1. customwere reacted for 65 h
  2. customPurification on a silica gel column with 1:1 ethyl acetate

Sources & evidence

ORD record
ord-9eb254b8d34f49e3b23c5ca57892e5d4
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

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