Ethanol → HCID 70179491, compound

HRID 2227183Notes

Reaction equation

HRID 2227183 reaction equation
[F:1][C:2]1[C:28]([F:29])=[C:27]([F:30])[C:5]2[N:6]([C@@H:13]3[O:25][C@H:24]([CH3:26])[C@@H:19]([O:20]C(=O)C)[C@H:14]3[O:15]C(=O)C)[C:7]([NH:9][CH:10]([CH3:12])[CH3:11])=[N:8][C:4]=2[CH:3]=1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+].O>CO>[F:1][C:2]1[C:28]([F:29])=[C:27]([F:30])[C:5]2[N:6]([C@@H:13]3[O:25][C@H:24]([CH3:26])[C@@H:19]([OH:20])[C@H:14]3[OH:15])[C:7]([NH:9][CH:10]([CH3:11])[CH3:12])=[N:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 10340Sodium CarbonateHCID 54410004HCID 54410004, compound

Product 1

HCID 70179491HCID 70179491, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5,6,7-Trifluoro-1-(2,3-di-O-acetyl-5-deoxy-beta-D-ribofuranosyl)-N-(1-methylethyl)-1H-benzimidazol-2-amine (0.41 g, 0.99 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 dichlormethane-methanol as eluant to provide a white solid (0.16 g, 47%); m.p. 175-178° C.: 1H NMR (DMSO-d6) δ: 7.17 (m, 1H, Ar—H), 6.78 (d, J=7.4, Hz, 1H, NH), 5.69 (dd, J=6.3, 1.8 Hz, 1H, CH), 5.26 (d, J=6.5 Hz, 1H, OH), 5.21 (d, J=5.2 Hz, 1H, OH), 4.15 (m, 1H, CH), 4.07 (m, 1H, CH), 3.86-3.74 (m, 2H, overlapping CH), 1.34 (d, J=6.3 Hz, 3H, CH3), 1.23 (d, J=6.5 Hz, 6H, overlapping CH3).

Workup

  1. customThe title compound was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b651fc5602c94b66b248961f0a3dea09
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

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