1,2-Dichloroethane → (E)-3-(6,6-dimethyl-7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)-N-methyl-N-((3-methylbenzofuran-2-yl)methyl)acrylamide

Participants

Reaction Conditions

Reaction Steps

EDC (102 mg, 0.53 mmol) was added to a suspension of (E)-3-(6,6-dimethyl-7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic acid hydrochloride (125 mg, 0.44 mmol), HOBt (66 mg, 0.49 mmol), N-methyl(3-methylbenzofuran-2-yl)methanamine (92 mg, 0.49 mmol) and (i-Pr)2EtN (0.37 mL, 2.2 mmol) in DMF (5 mL). The mixture was allowed to stir for 23 h at 40° C. The mixture was cooled to room temperature and diluted with water (20 mL) at 0° C. to yield a brown precipitate, which was collected by suction filtration. The solid was then triturated with diethyl ether to obtain an off-white solid product. Yield: 137 mg (81%); 1H NMR (300 MHz, DMSO-d6) δ 10.64 (s, 1H), 8.40 (s, 1H), 8.09 (s, 1H), 7.59-7.19 (m, 6H), 4.91 (s, 2H), 3.09 (s, 3H), 2.81 (s, 2H), 2.28 (s, 3H), 1.09 (s, 6H); ESI MS m/z 404 [C24H25N3O3+H]+.

Provenance & Evidence