Sodium hydride → 6-[2,6-dichloro-3-(5-chloro-2-thienyl)phenyl]-4-(2,2-difluoroethyl)-7-hydroxy[1,3]thiazolo[4,5-b]pyridin-5(4H)-one

Participants

Reaction Steps

120 mg (0.23 mmol) of methyl 4-[{[2,6-dichloro-3-(5-chloro-2-thienyl)phenyl]acetyl}(2,2-difluoroethyl)amino]-1,3-thiazole-5-carboxylate were dissolved in 10 ml of THF, and 6.6 mg (0.27 mmol) of sodium hydride were added under an atmosphere of argon. The reaction mixture was stirred at RT for 4 h. The THF was then removed under reduced pressure and the residue was taken up in water. The aqueous phase was extracted with dichloromethane, the organic phase was dried and concentrated by evaporation, the aqueous phase was acidified with 1N hydrochloric acid. After extraction with dichloromethane, the organic phase was dried and concentrated by evaporation. The product-containing residues were chromatographed (acetonitrile/water (0.05% trifluoroacetic acid) 20/80 to 100/0)). This gave 50 mg of 6-[2,6-dichloro-3-(5-chloro-2-thienyl)phenyl]-4-(2,2-difluoroethyl)-7-hydroxy[1,3]thiazolo[4,5-b]pyridin-5(4H)-one.

Provenance & Evidence