Methanol → HCID 54160967, compound

HRID 1167083Notes

Reaction equation

HRID 1167083 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

4-Bromo-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. Found: C, 39.42; H, 4.20; N, 9.05.

Workup

  1. customThe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-51b470f550684340bac8ee9fb3a6ea62
Source dataset
uspto-grants-2003_09
Patent number
US06617315B1

Reaction notes

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