Methyl chloroformate → HCID 86612784, compound

Participants

Reaction Steps

A solution of 1-(2-aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[2-(4-morpholinyl)ethyl]-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 (0.0087 mL, 0.11 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, filtered, washed with 2:1 Et2O:MeOH, and dried in vacuo to provide the title compound as a pale yellow solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.23 (s, 1 H), 3.06-3.20 (m, 2 H), 3.25-3.32 (m, 2 H), 3.36-3.43 (m, 2 H), 3.45 (s, 3 H), 3.55 (d, J=10.95 Hz, 2 H), 3.69 (t, J=12.2 Hz, 2 H), 3.78 (d, J=6.74 Hz, 2 H), 4.00 (d, J=12.35 Hz, 2 H), 4.15 (s, 2 H), 4.31 (t, J=5.76 Hz, 2 H), 7.12-7.19 (m, 2 H), 7.38-7.45 (m, 2 H), 8.16 (s, 1 H), 8.55 (s, 1 H), 9.91 (br. s., 1 H), 10.39 (t, J=6.60 Hz, 1 H); ES+ MS: 528 (M+H+).

Provenance & Evidence