HCID 53968866, compound → HCID 53814777, compound

HRID 2227198Notes

Reaction equation

HRID 2227198 reaction equation
[Br:1][C:2]1[N:6]([C@@H:7]2[O:19][C@H:18]([CH3:20])[C@@H:13]([O:14]C(=O)C)[C@H:8]2[O:9]C(=O)C)[C:5]2[CH:21]=[C:22]([C:25]([F:28])([F:27])[F:26])[CH:23]=[CH:24][C:4]=2[N:3]=1>CCOC(C)=O.CCCCCC>[Br:1][C:2]1[N:6]([C@@H:7]2[O:19][C@H:18]([CH3:20])[C@@H:13]([OH:14])[C@H:8]2[OH:9])[C:5]2[CH:21]=[C:22]([C:25]([F:26])([F:27])[F:28])[CH:23]=[CH:24][C:4]=2[N:3]=1

Participants

3

Reactant 1

HCID 53968866HCID 53968866, compound

Product 1

HCID 53814777HCID 53814777, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Starting with 2-bromo-6-trifluoromethyl-1-(2,3-di-O-acetyl-5-deoxy-beta-D-ribofuranosyl)-1H-benzimidazole, this compound was prepared according to general procedure III. Following two flash column chromatographic purifications on silica gel with EtOAc/hexane (3:2), a 14% yield of the title compound was obtained as a foam. 1H NMR (DMSO-d6) δ1.4 (d, 3H, Me), 3.8-3.9 (m, 1H, CH), 3.9-4.1 (m, 2H, 2×CH), 4.45 (q, 1H, CH), 5.3 (d, 1H, OH), 5.5 (d, 1H, OH), 5.91 (d,1H, CH), 7.6 (d, 1H, aromatic), 7.82 (d, 1H, aromatic), 7.9 (s, H, aromatic).

Workup

  1. customthis compound was prepared

Sources & evidence

ORD record
ord-767f80aae350486295ed06fc852f6eae
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

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