Water → 1-[2-(Acetylamino)ethyl]-N-[2-(ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Participants

Reaction Conditions

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 (0.020 g, 0.047 mmol) and diisopropyl ethylamine (0.041 mL, 0.24 mmol) in DMF (5 mL) under nitrogen was treated with acetic anhydride (0.0044 mL, 0.047 mmol) at ambient temperature. The reaction was warmed slightly to solubilize the reacted at ambient temperature for 10 min. Water was added (2 mL) and the reaction was cooled to 0° C. and concentrated in vacuo. The resulting residue was treated with 1 N NaHSO4 and filtered then triturated with Et2O and dried in vacuo to provide the title compound as an off-white solid: 1H NMR (300 MHz, DMSO-D6) δ ppm 1.1 (t, J=6.9 Hz, 3 H), 1.7 (s, 3 H), 3.3 (dd, J=12.5, 5.3 Hz, 2 H), 3.5 (q, J=7.0 Hz, 2 H), 3.5 (s, 4 H), 4.1 (s, 2 H), 4.3 (t, J=6.7 Hz, 2 H), 7.1 (t, J=9.0 Hz, 2 H), 7.4 (dd, J=8.4, 5.5 Hz, 2 H), 8.0 (t, J=5.6 Hz, 1 H), 8.2 (s, 1 H), 8.6 (s, 1 H), 10.4 (s, 1 H), 17.1 (s, 1 H); ES+ MS: 471 (M+H+).

Provenance & Evidence