1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 52950661, compound

Participants

Reaction Steps

3-(Furan-2-ylmethoxy)-azetidine hydrochloride (558 mg, 2.94 mmol), EDCI (563 mg, 2.94 mmol), HOBt (410 mg, 2.94 mmol) and diisopropylethylamine (853 μL, 4.9 mmol) were successively added to a solution of (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)-acrylic acid hydrochloride (500 mg, 1.96 mmol) in dimethylformamide (50 mL) at room temperature. The reaction mixture was stirred for 2 days and then diluted by addition of ethyl acetate (50 mL) and water (50 mL). The aqueous layer was separated and successively extracted with ethyl acetate (2×50 mL) and dichloromethane (2×50 mL). The combined organic phases were washed with a saturated solution of sodium chloride (3×60 mL), dried over sodium sulfate, filtered and concentrated to dryness. The residue was purified by chromatography on silica gel, using dichloromethane/methanol (10:0 to 95:5) as eluent. After trituration of the isolated solid in diethylether, the title product was obtained as a white solid (236 mg, 34%).

Provenance & Evidence