4-Aminopyridine → 2-{2-[7-Chloro-3-(3,5-dimethylphenyl)-2-oxo-6-(3-pyridin-4-yl-ureido)-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid benzyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-{2-[6-amino-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid benzyl ester (200 mg in 5 mL dry methylene chloride) at 0° C. was added phosgene (0.3 mL of a 1.93 M solution in toluene) followed by 0.111 mL of triethylamine and the mixture stirred for 1 hour at 0° C. At this time, 188 mg of 4-aminopyridine was added and the mixture allowed to warm to room temperature. After 20 hours, the mixture was diluted with ethyl acetate (200 mL) and the reaction quenched by the addition of 10% citric acid. The organic portion was concentrated in vacuo to provide the crude title compound.

Provenance & Evidence