Methanol → HCID 21356506, compound

HRID 1532602Notes

Reaction equation

HRID 1532602 reaction equation
[Br:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][CH:12]3[CH2:14][CH2:13]3)[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]3[CH2:13][CH2:14]3)[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 70023515HCID 70023515, compound

Product 1

HCID 21356506HCID 21356506, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Bromo-2-(cyclopropylamino)-5,6-dichloro-1-(2,3,5-tri-O-acetyl-beta-L-ribofuranosyl)-1H-benzimidazole (1.01 g, 1.74 mmol), sodium carbonate (0.265 g, 2.50 mmol), water (4 mL), methanol (5 mL), and ethanol (8 mL) were used according to general procedure III. The product was purified using silica gel chromatography using 10:1 dichloromethane/methanol to afford 0.28 g (36%) of a white solid: m.p. 205-208° C. Anal. calcd for C15H16Cl2BrN3O4-(0.25 C4H7O2): C, 40.45; H, 3.82; N, 8.84 Found: C, 40.38; H, 3.95; N, 8.90.

Workup

  1. customThe product was purified

Sources & evidence

ORD record
ord-ef313e760e1f4084a6fec48e4d13d94a
Source dataset
uspto-grants-2001_03
Patent number
US06204249B1

Reaction notes

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