N-(3-Aminopropyl)morpholine → 1-[2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[3-(4-morpholinyl)propyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide [3-(4-morpholinyl)propyl]amine

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 (0.025 g, 0.049 mmol) in EtOH (2.5 mL) under nitrogen was treated with [3-(4-morpholinyl)propyl]amine (0.035 mL, 0.24 mmol) for 40 min.@130° C. in a microwave vessel. The reaction was then cooled to ambient temperature and the resulting suspension was filtered, washed with EtOH and Et2O then thoroughly dried under high vacuum to provide the title compound as a white solid: 1H NMR (300 MHz, DMSO-D6) δ ppm 1.5 (m, 4 H), 2.2 (t, J=7.0 Hz, 2 H), 2.3 (m, 1 H), 2.6 (t, J=6.9 Hz, 2 H), 3.2 (q, J=6.5 Hz, 2 H), 3.5 (q, J=4.9 Hz, 8 H), 3.9 (t, J=5.5 Hz, 2 H), 4.1 (s, 2 H), 4.5 (t, J=5.6 Hz, 2 H), 7.1 (ddd, J=9.1, 6.7, 2.1 Hz, 2 H), 7.3 (m, 2 H), 7.8 (m, 4 H), 8.1 (s, 1 H), 8.4 (t, J=1.1 Hz, 1 H), 10.0 (t, J=6.0 Hz, 1 H); ES+ MS: 614 (M+H+).

Provenance & Evidence