Phosphorus oxychloride → HCID 59443566, compound

Participants

Reaction Conditions

Reaction Steps

Phosphorus oxychloride (190 mg, 1.2 mmol) was added to a solution of N-[2-(3,4-difluorophenyl)-2-oxoethyl]-3-[1-[(dimethylamino)sulfonyl]-4-(2,2-dimethylbutyl)-1H-imidazol-2-yl]propanamide (for synthesis see example 234) (30 mg, 0.06 mmol) in dry acetonitrile (4 mL) at rt. After stirring at 80° C. overnight, saturated sodium bicarbonate (ca. 3 mL) was added. The aqueous phase was washed with 1:5 ethyl acetate/diethyl ether, basified with 5N aqueous sodium hydroxide and extracted with ethyl acetate. Combined extracts were washed with brine, dried (sodium sulfate) and concentrated to give a residue. The residue was dissolved in methylene chloride to give the title compound, which was acidified with 1M HCl in diethyl ether. Additional diethyl ether and hexane were added, and concentration afforded the HCl salt of the title compound. LC-MS: m/e 360 (M+H).

Provenance & Evidence