N-methyl-2-pyrrolidone → HCID 86661294, compound

Participants

Reaction Steps

An N-methylpyrrolidinone (5 mL) solution of ethyl 2-(2-aminothiazol-4-yl)-2-oxoacetate (commercial, 1.00 g, 5.0 mmol) and 1-fluoro-3-(isocyanatomethyl)benzene (831 mg, 5.5 mmol) was heated in a microwave reactor at 120 C for 30 minutes. Upon cooling, water (50 mL) was added with vigorous stiffing. Filtration of the precipitate afforded ethyl 2-(2-(3-(3-fluorobenzyl)ureido)thiazol-4-yl)-2-oxoacetate. M/Z 352 (M+H)+. The filtrate was dissolved in EtOH (100 mL) then hydroxylamine hydrochloride (700 mg, 10 mmol) and sodium acetate (1.07 g, 13 mmol) were added to the mix. The solution was stirred at 75 C for 4 hours and filtered while hot. Evaporation of the mixture and Flash chromatography afforded ethyl 2-(2-(3-(3-fluorobenzyl)ureido)thiazol-4-yl)-2-(hydroxyimino)acetate as a mixture of isomers. M/Z 367 (M+H)+.

Provenance & Evidence