Methanol → HCID 54160967, compound

HRID 1532600Notes

Reaction equation

HRID 1532600 reaction equation
[Br: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]=[C:4]([Cl:33])[C:3]=1[Cl:34].C(=O)([O-])[O-].[Na+].[Na+].O.CO>C(O)C>[Br: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]=[C:4]([Cl:33])[C:3]=1[Cl:34]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 10340Sodium CarbonateHCID 70022127HCID 70022127, compound

Product 1

HCID 54160967HCID 54160967, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4Bromo-5,6-dichloro-2-(isopropylamino)-1-(2,3,5-tri-O-acetyl-beta-L-ribofuranosyl)-1H-benzimidazole (1.16 g, 2.0 mmol), sodium carbonate (0.28 g, 2.64 mmol), water (4 mL), methanol (6 mL), and ethanol (8 mL) were used according to general procedure III. The product was purified by silica gel chromatography using 10:1 dichloromethane/methanol to afford 0.64 g (70%) of a white powder, m.p. 221-222° C. Anal. Calcd for C15H18BrCl2N3O4: C, 39.59; H, 3.99; N, 9.23. Pound: C, 39.42; H, 4.20; N, 9.05.

Workup

  1. customThe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-4c565e89edee49739f466faa4ab38dba
Source dataset
uspto-grants-2001_03
Patent number
US06204249B1

Reaction notes

Loading…