Salicylamide → HCID 57642865, compound

Participants

Reaction Conditions

Reaction Steps

Salicylamide (0.056 g), cesium carbonate (0.130 g), 2,2,6,6-tetramethyl-3,5-heptanedione (0.005 mL), and copper(I) chloride (0.010 g) were added to a solution of 4-[3-benzyl-7-bromo-1-(2-cyanobenzyl)-2-oxo-1H-imidazo[4.5-c]pyridin-4-yl]-piperazine-1-car boxylic acid t-butyl ester (0.123 g) in 1-methyl-2-pyrolidone (2 mL). This was then heated at 130° C. for 22 hours under a nitrogen atmosphere. The reaction solution was cooled, t-butyl methyl ether was added, and this was filtered through celite. The celite was washed with ethyl acetate (25 mL), and the organic layers were combined, and then washed sequentially with 2 N hydrochloric acid (10 mL), 0.5 N hydrochloric acid (10 mL), 1 N aqueous sodium hydroxide solution (10 mL), and saturated aqueous sodium chloride solution (10 mL). This was then dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by reverse phase high performance liquid chromatography to give the title compound (0.023 g).

Provenance & Evidence