Pyridine → 2-{2-[3-(3-Bromophenyl)-7-chloro-6-(3-cyclopropyl-ureido)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-{2-[6-amino-3-(3-bromophenyl)-7-chloro-2-oxo-1,2-dihydroquinolin-4-yloxy]-1-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (20 mg in 1.0 mL methylene chloride) at 0° C. was added 0.009 mL pyridine followed by 4 mg triphosgene and the mixture allowed to stir at 0° C. for 1 hour. At this time 0.012 mL of cyclopropylamine was added via syringe and the reaction mixture warmed to room temperature. After 2 hours, the mixture was diluted with 20 mL ethyl acetate and washed with saturated ammonium chloride (10 mL) and brine (10 mL). The organic portion was dried over magnesium sulfate then concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (hexane:ethyl acetate, 2:1; then 1:1; then 0:1) to give the title compound (14 mg).

Provenance & Evidence