Chloride → 1-(2-{[(Dimethylamino)carbonyl]amino}ethyl)-N-[2-(ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Participants

Reaction Steps

A solution of 1-(2-aminoethyl)-N-[2-(ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (0.02 g, 0.047 mmol) and diisopropyl ethylamine (0.041 mL, 0.24 mmol) in DMF (5 mL) under nitrogen was treated with N,N-dimethyl carbonyl chloride (0.0043 mL, 0.047 mmol) at ambient temperature. After 2 h, an additional 0.001 mL of the chloride was added and the was stirred at ambient temperature for an additional 6 h. The reaction was concentrated in vacuo and the resulting residue suspended in DMSO and water, filtered, then washed with water and Et2O before drying in vacuo to provide the title compound as an off-white solid: 1H NMR (400 MHz, DMSO-D6) δ ppm 1.1 (t, J=7.0 Hz, 3 H), 2.7 (s, 6 H), 3.3 (d, J=7.0 Hz, 2 H), 3.5 (q, J=7.0 Hz, 2 H), 3.5 (s, 4 H), 4.1 (s, 2 H), 4.2 (t, J=6.1 Hz, 2 H), 6.6 (m, 1 H), 7.1 (t, J=8.9 Hz, 2 H), 7.4 (dd, J=8.8, 5.5 Hz, 2 H), 8.3 (s, 1 H), 8.5 (s, 1 H), 10.4 (s, 1 H); ES+ MS: 500 (M+H+).

Provenance & Evidence