Pyridine → HCID 54053710, compound

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-ylsulfanyl]-ethyl }-piperidine-1-carboxylic acid benzyl ester (23 mg in 1.0 mL methylene chloride) at 0° C. was added 0.01 mL pyridine followed by phosgene (0.03 mL of a 1.93M solution in toluene) and the mixture allowed to stir at 0° C. for 1 hour. At this time 0.02 mL of cyclopropylamine was added via syringe and the reaction mixture warmed to room temperature. After 4 hours, the mixture was diluted with ethyl acetate and washed sequentially with 10% aqueous sodium bisulfate, water and brine. The organic portion was dried over magnesium sulfate then concentrated in vacuo. Purification of the crude material by flash chromatography on silica gel (chloroform:methanol, 95:5) gave the title compound (18 mg).

Provenance & Evidence