1,2-Dichloroethane → N-methyl-(1H-indol-2-ylmethyl)-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]napthyridin-3-yl)acrylamide

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Reaction Steps

EDC (498 mg, 2.6 mmol) was added to a solution of 3-methyl-2-(methylaminomethyl)indole (348 mg, 2.0 mmol), 3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-acrylic acid hydrochloride (533 mg, 2.1 mmol), HOBT.H2O (270 mg, 2.0 mmol) and DIPEA (1.04 mL, 6 mmol) in DMF (5 mL). After stirring overnight, the mixture was slowly diluted with water (50 mL). The resulting precipitate was collected by filtration washed with water and dried. The precipitate was suspended in MeOH (10 mL), stirred for 60 hours, filtered and dried to afford title compound (203 mg, 27%). 1H NMR (300 MHz, DMSO-d6, 8): 10.77 and 10.58 (rotamers, 2s, br, 1H), 10.64 (s, br, 1H), 8.37 (d, J=1.9 Hz, 1H), 8.08 (s, 1H), 7.58-6.92 (m, 6H), 4.91 and 4.75 (rotamers, 2s, 2H), 3.09 and 2.91 (rotamers, 2s, 3H), 2.90 (m, 2H), 2.53, (m, 2H), 2.25 (s, 3H). MS (ESI): m/e 375 (M+H)+.

Provenance & Evidence