Water → 1-(2-Aminoethyl)-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-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-N-[2-(ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (0.155 g, 0.277 mmol) in EtOH (6.5 mL) under nitrogen was treated with hydrazine (0.218 mL, 6.92 mmol) for 7 h@50° C. The reaction was then cooled to ambient temperature and stirred overnight. After heating an additional 6.5 h@50° C. the resulting solution was poured into water (75 mL), refrigerated and the resulting suspension was filtered and washed with cold 3:1 water:EtOH. The solid was then thoroughly dried under high vacuum to provide the title compound as an off-white solid: 1H NMR (400 MHz, DMSO-D6) δ ppm 1.1 (t, J=7.1 Hz, 3 H), 2.8 (t, J=7.2 Hz, 2 H), 3.5 (q, J=6.9 Hz, 2 H), 3.5 (s, 4 H), 4.2 (s, 2 H), 4.2 (t, J=7.1 Hz, 2 H), 7.1 (t, J=8.8 Hz, 2 H), 7.4 (dd, J=8.7, 5.4 Hz, 2 H), 8.1 (s, 1 H), 8.5 (s, 1 H), 10.4 (s, 1 H); ES+ MS: 429 (M+H+).

Provenance & Evidence