Trimethylsilyl triflate → 4,6-Dichloro-2-(isopropylamino)-1-(2,3,5-tri-O-acetyl-beta-L-ribofuranosyl)benzimidazole

HRID 1532608Notes

Reaction equation

HRID 1532608 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][CH:12]([CH3:14])[CH3:13])[NH:7][C:6]=2[CH:5]=[C:4]([Cl:15])[CH:3]=1.C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.C(O[CH:44]1[O:56][C@H:55]([CH2:57][O:58][C:59](=[O:61])[CH3:60])[C@@H:50]([O:51][C:52](=[O:54])[CH3:53])[C@H:45]1[O:46][C:47](=[O:49])[CH3:48])(=O)C>ClCCCl>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([NH:11][CH:12]([CH3:13])[CH3:14])[N:7]([C@H:44]3[O:56][C@@H:55]([CH2:57][O:58][C:59](=[O:61])[CH3:60])[C@H:50]([O:51][C:52](=[O:54])[CH3:53])[C@@H:45]3[O:46][C:47](=[O:49])[CH3:48])[C:6]=2[CH:5]=[C:4]([Cl:15])[CH:3]=1

Participants

6

Reactant 4

HCID 65367Trimethylsilyl triflateHCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 9797055D-Ribofuranose, 1,2,3,5-tetraacetateHCID 229954404,6-Dichloro-N-(propan-2-yl)-1H-benzimidazol-2-amine

Product 1

HCID 572760474,6-Dichloro-2-(isopropylamino)-1-(2,3,5-tri-O-acetyl-beta-L-ribofuranosyl)benzimidazoleYield 37%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

4,6-Dichloro-2-(isopropylamino)-1H-benzimidazole (0.83 g, 3.40 mmol), N,O-bis(trimethylsilyl)acetamide (0.88 mL, 0.72 g, 3.56 mmol), trimethylsilyl trifluoromethanesulfonate (0.43 mL, 0.49 g, 2.20 mmol), 1,2,3,5-tetra-O-acetyl-ribofuranose (1.31 g, 4.12 mmol) and 1,2-dichloroethane (10 mL) were used according to general procedure II. The product was purified by silica gel chromatography using 60:1 dichloromethane/methanol to afford 0.63 g (37%) of a white foam. MS (CI): m/z 502.1 (M+H).

Workup

  1. customThe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-862e4bd8614b4e20bb15ca997339d77a
Source dataset
uspto-grants-2001_03
Patent number
US06204249B1

Reaction notes

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