Methanol → 4-Chloro-2-(isopropylamino)-1-(beta-L-ribofuranosyl)-1H-benzimidazole

HRID 1167088Notes

Reaction equation

HRID 1167088 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][CH:12]([CH3:14])[CH3:13])[N:7]([C@H:15]3[O:27][C@@H:26]([CH2:28][O:29]C(=O)C)[C@H:21]([O:22]C(=O)C)[C@@H:16]3[O:17]C(=O)C)[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].O.CO>C(O)C>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][CH:12]([CH3:14])[CH3:13])[N:7]([C@H:15]3[O:27][C@@H:26]([CH2:28][OH:29])[C@H:21]([OH:22])[C@@H:16]3[OH:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 10340Sodium CarbonateHCID 572936104-Chloro-2-(isopropylamino)-1-(2,3,5-tri-O-acetyl-beta-L-ribofuranosyl)-1H-benzimidazole

Product 1

HCID 571249734-Chloro-2-(isopropylamino)-1-(beta-L-ribofuranosyl)-1H-benzimidazoleYield 68.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Chloro-2-(isopropylamino)-1-(2,3,5-tri-O-acetyl-beta-L-ribofuranosyl)-1H-benzimidazole (2.24 g, 4.79 mmol), sodium carbonate (0.67 g, 6.32 mmol), water (7 mL), methanol (14 mL) and ethanol (20 mL) were used according to general procedure III. The product was purified by silica gel chromatography using 10:1 dichloromethane/methanol to afford 1.12 g (68%) of a white solid: m.p. 225-227° C. Anal. calcd for C15H20ClN3O4: C, 52.77; H, 5.91; N, 12.32. Found: C, 52.79; H, 5.96; N, 12.25.

Workup

  1. customThe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-73e700317ac64ab2825a3c164600d21b
Source dataset
uspto-grants-2003_09
Patent number
US06617315B1

Reaction notes

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