Hydrazine → 1-(2-Aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

A solution of 1-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxyethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (0.255 g, 0.48 mmol) in EtOH (80 mL) under nitrogen was treated with hydrazine (0.151 mL, 4.81 mmol) for 1 h@50° C. Additional hydrazine was added (0.075 mL @1 h) after 1 and 4 hours (0.15 mL @ 4 h) and the reaction was stirred for a total of 8 h@50° C. The reaction was then capped and cooled in a refrigerator overnight. The resulting suspension was filtered then thoroughly dried under high vacuum to provide the title compound as an off-white solid: 1H NMR (300 MHz, DMSO-D6) δ ppm 2.8 (m, 1 H), 3.4 (m, 2 H), 3.6 (m, 2 H), 4.1 (s, 2 H), 4.2 (m, 2 H), 4.9 (bs, 1 H), 7.1 (t, J=8.7 Hz, 2 H), 7.4 (m, 2 H), 8.1 (s, 1 H), 8.5 (s, 1 H), 10.5 (m, 1 H); ES+ MS: 401 (M+H+).

Provenance & Evidence