Benzimidazole → HCID 54186712, compound

HRID 1281674Notes

Reaction equation

HRID 1281674 reaction equation
[Cl:1][C:2]1[C:3]([CH3:29])=[CH:4][C:5]2[N:9]=[CH:8][N:7]([C@@H:10]3[O:27][CH2:26][C@@H:21]([O:22][C:23](=[O:25])[CH3:24])[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]3[O:12][C:13](=[O:15])[CH3:14])[C:6]=2[CH:28]=1.[Br:30]N1C(=O)CCC1=O.N1C2C=CC=CC=2NC=1>O1CCCC1>[Br:30][C:8]1[N:7]([C@@H:10]2[O:27][CH2:26][C@@H:21]([O:22][C:23](=[O:25])[CH3:24])[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]2[O:12][C:13](=[O:15])[CH3:14])[C:6]2[CH:28]=[C:2]([Cl:1])[C:3]([CH3:29])=[CH:4][C:5]=2[N:9]=1

Participants

5

Reactant 3

HCID 5798BenzimidazoleHCID 67184N-bromobutanimideHCID 69946241HCID 69946241, compound

Product 1

HCID 54186712HCID 54186712, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared according to General Procedure IV using 6-Chloro-5-methyl-(2,3,4-tri-O-acetyl-beta-D-ribopyranosyl)-1H-benzimidazole (0.37 g, 0.87 mmol), 30 ml tetrahydrofuran (Aldrich Sure Seal, Milwaukee), and a total of 1.2 g (7.0 mmol) of N-bromosuccinimide that was added in ca 0.2 equivalents/benzimidazole every 15 min over 1 h. The product from work-up by General Procedure IV was purified on a silica gel column (2.5×20 cm, 230-400 mesh) with dichloromethane containing 0.5% methanol to give 2-Bromo-6-chloro-5-methyl-(2,3,4-tri-O-acetyl-beta-D-ribopyranosyl)-1H-benzimidazole (0.33 g, 0.66 mmol, 75%); MS (ES+): m/z (rel. intensity) 526 (1.0, M+23 (Na)); 1H NMR (DMSO-d6) δ8.18 (s,1H), 7.62 (s, 1H), 5.97-5.904(d, 1H, J=9.4 Hz), 5.78-5.60 (m, 3H), 4.20-4.10 (m, 1H), 4.05-3.97 (m, 1H) 2.41 (s, 3H), 2.25 (s, 3H), 2.04 (s, 3H), 1.78 (s, 3H)

Workup

  1. customThe title compound was prepared
  2. customThe product from work-up by General Procedure IV was purified on a silica gel column (2.5×20 cm, 230-400 mesh) with dichloromethane containing 0.5% methanol

Sources & evidence

ORD record
ord-2566d271b9f64c78ae2bd673a3fcd374
Source dataset
uspto-grants-2002_09
Patent number
US06455507B1

Reaction notes

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