Hydrazine → HCID 69482715, compound

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 (0.252 g, 0.49 mmol) in EtOH (15 mL) under nitrogen was treated with 2-[(2-aminoethyl)oxy]ethanol (0.176 mL, 2.44 mmol) for 15 min.@150° C. in a microwave vessel. Transferred the mixture to a test tube, diluted with EtOH (30 mL), and treated with hydrazine (0.4 mL, 13 mmol)@50° C. overnight. After the reaction was cooled to ambient temperature the resulting suspension was diluted with water (120 mL) and refrigerated overnight. The resulting suspension was filtered, washed with 2:1 water:EtOH and thoroughly dried under high vacuum to provide the title compound as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 2.27 (s, 1 H), 2.79 (t, J=6.81 Hz, 2 H), 3.45-3.61 (m, 8 H), 4.12-4.17 (m, 2 H), 4.22 (t, J=6.74 Hz, 2 H), 4.62 (s, 1 H), 7.10-7.18 (m, 2 H), 7.33-7.42 (m, 2 H), 8.07-8.16 (m, 1 H), 8.46-8.54 (m, 1 H), 10.44 (t, J=5.19 Hz, 1 H); ES+ MS: 445 (M+H+).

Provenance & Evidence