Pyridine → HCID 58443370, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydroquinolin-2(1H)-one (cilostazol, 1, A=H, 15.00 g, 40.6 mmol), pyridine (6.42 g, 81.2 mmol) and 4-dimethyl-aminopyridine (DMAP, 6.45 g, 52.8 mmol) in 135 mL chloroform at room temperature is added slowly 4-chlorobutanoyl chloride (7.45 g, 52.8 mmol). The mixture is stirred at 70° C. for 20 hours. The reaction mixture is diluted with 1000 mL CH2Cl2, and washed with 1N HCl, saturated NaHCO3 solution and brine. The organic phase is dried over sodium sulphate, and concentrated. The residue is purified by flash chromatography (silica gel, CH2Cl2/tert-butyl methyl ether 90:10) to give the title compound in 42% yield.

Provenance & Evidence