Methanesulfonyl chloride → HCID 69482689, 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 methanesulfonyl chloride (0.0053 mL, 0.068 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 an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 2.35-2.46 (m, 2 H), 2.90 (s, 3 H), 3.06-3.20 (m, 1 H), 3.21-3.29 (m, 2 H), 3.34-3.45 (m, 2 H), 3.52-3.68 (m, 4 H), 3.72-3.83 (m, 2 H), 3.97-4.02 (m, 1 H), 4.15 (d, J=0.56 Hz, 2 H), 4.30-4.41 (m, 2 H), 7.13 (t, J=8.98 Hz, 2 H), 7.29 (s, 1 H), 7.41 (dd, J=8.84, 5.62 Hz, 2 H), 8.13 (s, 1 H), 8.56 (s, 1 H), 9.83 (br. s., 1 H), 10.32-10.41 (m, 1 H); ES+ MS: 548 (M+H+).

Provenance & Evidence