4-Methylmorpholine → N-{4-[(2-methylpropyl)amino]quinolin-3-yl}-3-(2-methyl-1,3-dioxolan-2-yl)propanamide

Participants

Reaction Steps

To a cooled solution of N4-(2-methylpropyl)quinoline-3,4-diamine (2.15 g, 10 mmol) in DMF (40 mL) was added 3-(2-methyl-1,3-dioxolan-2-yl)propanoic acid (2.40 g, 15 mmol), followed by 4-methylmorpholine (1.6 mL, 15 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) (2.9 g, 15 mmol). The resulting suspension was stirred at room temperature and 4-dimethylaminopyridine (0.12 g, 1 mmol) was added. The dark yellow solution was stirred at room temperature for 16 hours, then saturated aqueous sodium bicarbonate (100 mL) was added. The mixture was transferred to a separatory funnel and was extracted with dichloromethane (2×100 mL). The organic layers were combined, washed with saturated aqueous sodium bicarbonate (100 mL) and brine (100 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford an oil that was purified by flash chromatography (silica gel, elution with 5% methanol in dichloromethane) to provide 2.55 g of N-{4-[(2-methylpropyl)amino]quinolin-3-yl}-3-(2-methyl-1,3-dioxolan-2-yl)propanamide.

Provenance & Evidence