Hydrochloric Acid → HCID 18467098, compound

Participants

Reaction Steps

To a solution of N-[1-butyl-4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridin-3-yl]-N′-[2,6-diisopropyl-4-(3-pyridylmethylamino)-phenyl]urea (476 mg, 0.752 mmol) in methanol (5 ml) are added a 37% aqueous formaldehyde solution (122 mg, 1.50 ml) and conc. hydrochloric acid (0.13 ml, 1.50 ml) at room temperature. The mixture is cooled with ice, and the thereto is added sodium cyanoborohydride (71.0 mg, 1.13 ml), and the mixture is stirred at room temperature for 5 hours. To the mixture is added water, and the mixture is extracted with ethyl acetate. The organic layer is extracted twice with sodium hydrogen carbonate, and dried over anhydrous magnesium sulfate. The solvent is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography to give the title compound (445 mg, 0.684 mmol) as colorless amorphous.

Provenance & Evidence