Ethyl Acetate → (E)-6-[3-(3-Isobutoxyazetidin-1-yl)-3-oxoprop-1-enyl]-3,4-dihydro-1,8-naphthyridin-2(1H)-one

Participants

Reaction Steps

3-Isobutoxyazetidine hydrochloride (98 mg, 0.6 mmol), EDCI (113 mg, 0.6 mmol), HOBt (80 mg, 0.6 mmol) and diisopropylethylamine (170 μL, 1.0 mmol) were successively added to a solution of 3-(chloromethyl)-1-methyl-1H-pyrazole (100 mg, 0.4 mmol) in dimethylormamide (10 mL) at room temperature. The reaction mixture was stirred over a week-end and then diluted by addition ethyl acetate (20 mL) and water (2×20 mL). The aqueous layer was separated and extracted with ethyl acetate (2×20 mL). The combined organic phases were washed with a saturated solution of sodium chloride (3×20 mL), dried over sodium sulfate, filtered and concentrated to dryness. The residue was purified by chromatography on silica gel, using dichloromethane/methanol (98:2 to 92:8) as eluent. The title product was obtained as a white solid (40 mg, 31%).

Provenance & Evidence