Hydrazine → HCID 69482180, 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-(4-morpholinyl)ethanamine (0.321 mL, 2.44 mmol) for 30 min. (150° C. in a microwave vessel. The reaction was further microwaved for an additional 30 min.@150° C. after the addition of another equivalent (0.064 mL) of the amine. The reaction was transferred 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 a pale yellow solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 2.27 (s, 1 H), 2.39-2.46 (m, 5 H), 2.70-2.81 (m, 2 H), 3.40-3.53 (m, 1 H), 3.57-3.61 (m, 6 H), 4.16 (s, 2 H), 4.18-4.26 (m, 2 H), 7.10-7.17 (m, 2 H), 7.35-7.41 (m, 2 H), 8.13-8.15 (m, 1 H), 8.50-8.51 (m, 1 H), 10.36-10.43 (m, 1 H); ES+ MS: 470 (M+H+).

Provenance & Evidence