Ethoxyethylamine → 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

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 (0.021 g, 0.041 mmol) in EtOH (2 mL) under nitrogen was treated with Ethoxyethylamine (0.021 mL, 0.2 mmol) for 10 min.@150° C. in a microwave vessel then@180° C. for an additional 10 min. After the reaction was cooled to ambient temperature the resulting suspension was filtered, and the filtered solid was washed with water and Et2O then thoroughly dried under high vacuum to provide the title compound as a beige solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.07 (t, J=6.95 Hz, 4 H), 1.56-1.91 (m, 1 H), 3.34-3.41 (m, 7 H), 3.88-3.92 (m, 2 H), 4.11 (s, 2 H), 4.53-4.56 (m, 1 H), 7.12-7.13 (m, 1 H), 7.32-7.37 (m, 2 H), 7.81-7.82 (m, 4 H), 8.14-8.15 (m, 1 H), 8.52 (dd, J=1.47, 0.35 Hz, 1 H), 9.76-10.16 (m, 1 H); ES+ MS: 559 (M+H+).

Provenance & Evidence