Dimethylformamide → HCID 86762323, compound

Participants

Reaction Steps

A solution of 1-(2-aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[3-(4-morpholinyl)propyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (0.025 g, 0.052 mmol) and diisopropyl ethylamine (0.05 mL, 0.29 mmol) in DMF (5 mL) under nitrogen was treated with methyl chloroformate (0.008 mL, 0.07 mmol) at 40° C. for 1 h then 3½ h at ambient temperature. The reaction was concentrated in vacuo and the resulting residue was triturated with Et2O:MeOH, and concentrated again in vacuo, before triturating again with EtOAc. Filtered the resulting suspension and dried in vacuo to provide the title compound as an orange solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.23-1.29 (m, 2 H), 1.99-2.05 (m, 1 H), 3.04-3.08 (m, 2 H), 3.10-3.19 (m, 7 H), 3.42 (s, 2 H), 3.44-3.49 (m, 6 H), 3.70 (t, J=11.81 Hz, 2 H), 3.96 (d, J=13.19 Hz, 2 H), 4.14 (s, 2 H), 4.29 (t, J=6.59 Hz, 2 H), 6.81 (t, J=4.67 Hz, 1 H), 7.14 (t, J=8.79 Hz, 2 H), 7.42 (dd, J=8.70, 5.59 Hz, 2 H), 8.32 (s, 1 H), 8.55 (d, J=1.28 Hz, 1 H), 10.15 (s, 1 H), 10.37 (t, J=6.50 Hz, 1 H); ES+ MS: 597 (M+H+).

Provenance & Evidence