HCID 54366639, compound → HCID 53968866, compound

HRID 2227197Notes

Reaction equation

HRID 2227197 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[CH:9][N:8]([C@@H:11]3[O:23][C@H:22]([CH3:24])[C@@H:17]([O:18][C:19](=[O:21])[CH3:20])[C@H:12]3[O:13][C:14](=[O:16])[CH3:15])[C:7]=2[CH:25]=1.[Br:28]C1N([C@@H]2O[C@H](C)[C@@H](OC(=O)C)[C@H]2OC(=O)C)C2C=CC(C(F)(F)F)=CC=2N=1>CCOC(C)=O.CCCCCC>[Br:28][C:9]1[N:8]([C@@H:11]2[O:23][C@H:22]([CH3:24])[C@@H:17]([O:18][C:19](=[O:21])[CH3:20])[C@H:12]2[O:13][C:14](=[O:16])[CH3:15])[C:7]2[CH:25]=[C:3]([C:2]([F:1])([F:26])[F:27])[CH:4]=[CH:5][C:6]=2[N:10]=1

Participants

4

Reactant 2

HCID 54366639HCID 54366639, compoundHCID 57236497HCID 57236497, compound

Product 1

HCID 53968866HCID 53968866, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Starting with 6-trifluoromethyl-1-(2,3-di-O-acetyl-5-deoxy-beta-D-ribofuranosyl)-1H-benzimidazole, this compound was prepared in a manner analogous to that described for 2-bromo-5-trifluoromethyl-1-(2,3-di-O-acetyl-5-deoxy-beta-D-ribofuranosyl)-1H-benzimidazole. Following flash column chromatography on silica with EtOAc/hexane (2:3), a 52% yield of the title compound was obtained as an oil. 1H NMR (DMSO-d6) δ1.48 (d, 3H, CH3), 2 (s, 3H, COCH3), 2.1 (s, 3H, COCH3), 4.2-4.3 (m, 1H, CH), 5.2 (t, 1H, CH), 5.63 (t, 1H, CH), 6.22 (d, 1H, CH), 7.6 (d, 1H, aromatic), 7.8 (d, 1H, aromatic), 8.1 (s, 1H, aromatic).

Workup

  1. customthis compound was prepared in a manner analogous to

Sources & evidence

ORD record
ord-49814637567941d8904c83c0ac967325
Source dataset
uspto-grants-2002_07
Patent number
US06413938B1

Reaction notes

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