Dimethyl Sulfoxide → HCID 178494118, compound

Participants

Reaction Steps

The product of example 11 (7.76 g, 21 mmol) was dissolved with warming in DMSO (105 mL) while stirring under argon. Cooling to room temperature and addition of triethylamine (29 mL, 208 mmol) resulted in two phases. The mixture was cooled with stirring to 18° C. in a water bath. The sulfur trioxide pyridine complex (13.4 g, 84 mmol) in DMSO (42 mL) was added dropwise over 15 min. The mild exotherm was controlled by adding ice to the water bath. The maximum internal temperature was 20° C. After the addition was complete, the mixture was stirred for 15 min., diluted with ethyl acetate (800 mL) and extracted four times with water (500 mL). The organic phase was dried over anhydrous sodium sulfate, filtered, and evaporated on a rotary evaporator to give 7.9 g of a crude product which NMR indicated contained −5% of the title compound. The remainder of the crude material was mostly 5-[4-(2-methoxy)pyrimidinyl]-4-(4-fluorophenyl)-1-(4-oxocyclohexyl)imidazole. Careful chromatography on silica gel (700 g) eluted with 0.5-3% methanol in methylene chloride gave the title product as a white solid (0.368 g, 4%). MS(ES+) [M+H]+, 429.

Provenance & Evidence