Hydrazine → 1-(2-Aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-{2-[(1-methylethyl)oxy]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Participants

Reaction Steps

A solution of ethyl 1-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (0.143 g, 0.28 mmol) in EtOH (3 mL) under nitrogen was treated with 2-[(1-methylethyl)oxy]ethanamine (0.102 mL, 0.83 mmol) for 50 min. (130° C. in a microwave vessel. The reaction was transferred to a test tube, diluted with EtOH (35 mL), and treated with hydrazine (0.174 mL, 5.55 mmol) for 4 h@50° C. After the reaction was cooled to ambient temperature the resulting suspension was diluted with water (150 mL) and refrigerated overnight. The resulting suspension was filtered, washed with 3:1 water:EtOH and 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 (d, J=6.2 Hz, 6 H), 2.8 (bs, 2 H), 3.3 (s, 2 H), 3.5 (m, 4 H), 3.6 (m, 1 H), 4.2 (s, 2 H), 7.1 (t, J=9.3 Hz, 2 H), 7.4 (dd, J=8.5, 5.4 Hz, 2 H), 8.1 (s, 1 H), 8.5 (s, 1 H), 10.4 (s, 1 H); ES+ MS: 443 (M+H+).

Provenance & Evidence