6-Chloronicotinic acid → 6-chloro-N-((7-chloro-4-oxo-1-phenyl-1,4-dihydroquinolin-3-yl)methyl)nicotinamide

Participants

Reaction Steps

To a stirred solution of 6-chloronicotinic acid (183 mg, 1.16 mmol) and N,N-diisopropylethylamine (409 mg, 552 μL, 3.16 mmol) in methylene chloride was added (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphonate (BOP) (559 mg, 1.26 mmol). After 15 min., 3-(aminomethyl)-7-chloro-1-phenylquinolin-4(1H)-one (intermediate D) (300 mg, 1.05 mmol) was added. After 1.5 hr., the suspension was diluted with CH2Cl2 and washed with water followed by citric acid solution (5%) and finally potassium carbonate solution. The organic layer was dried, filtered and concentrated to afford 6-chloro-N-(7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinolin-3-ylmethyl)-nicotinamide (340 mg, 76%). The product was used in subsequent reactions without further purification.

Provenance & Evidence