Ethanol → HCID 57002719, compound

HRID 2227182Notes

Reaction equation

HRID 2227182 reaction equation
[F: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]([CH3:28])[C@@H:21]([O:22]C(=O)C)[C@H:16]3[O:17]C(=O)C)[C:6]=2[CH:5]=[C:4]([F:29])[C:3]=1[F:30].C(O)C.C(=O)([O-])[O-].[Na+].[Na+].O>CO>[F: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]([CH3:28])[C@@H:21]([OH:22])[C@H:16]3[OH:17])[C:6]=2[CH:5]=[C:4]([F:29])[C:3]=1[F:30]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 10340Sodium CarbonateHCID 54145341HCID 54145341, compound

Product 1

HCID 57002719HCID 57002719, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4,5,6-Trifluoro-1-(2,3-di-O-acetyl-5-deoxy-beta-D-ribofuranosyl)-N-(1-methylethyl)-1H-benzimidazol-2-amine (0.42 g, 1.02 mmol), ethanol (10 mL), sodium carbonate (0.19 g, 1.79 mmol), water (2 mL) and methanol (5 mL) were used according to general procedure III. The title compound was purified by silica gel chromatography using 10:1 dichloromethane-methanol as eluant to provide a white solid (0.26 g, 75%); m.p. 148-151° C.; 1H NMR (DMSO-d6) δ: 7.10 (m, 1H, Ar—H), 6.68 (d, J=7.5 Hz, NH), 5.70 (d, J=6.7 Hz, 1H, CH), 5.27 (m, 2H, overlapping OH), 4.35 (dd, J=6.6 Hz, 1H, CH), 4.12 (m, 1H, CH), 3.91 (m, 1H, CH), 3.85 (m, 1H, CH), 1.40 (d, J=6.5 Hz, 3H, CH3), 1.24 (d, J=6.4 Hz, 6H, overlapping CH3).

Workup

  1. customThe title compound was purified by silica gel chromatography

Sources & evidence

ORD record
ord-8585a31a957d4388bb2575450fd0e5d7
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

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