A mixture of 3-(4-carboxybenzyl)-7-chloro-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxylic acid methyl ester (167 mg, 0.37 mmol), 2-aminoethanol (34 mg, 0.56 mmol), HOBt (50 mg), EDCI (142 mg, 0.74 mmol) and DIPEA (0.5 mL) in DCM (10 mL) and DMF (0.4 mL) was stirred at RT for 2 h. The reaction mixture was then partitioned between water and EtOAc. The organic layer was separated, washed twice with water, dried over Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified twice by flash chromatography to afford 7-chloro-3-[4-(2-hydroxyethylcarbamoyl)-benzyl]-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester (99 mg) as an off-white powder. MS=491 [M+H]+; MP=162-163.5° C.
