Methanesulfonyl chloride → HCID 69482601, 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 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 a pale yellow solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.67 (s, 1 H), 1.99 (br. s., 2 H), 2.90 (s, 3 H), 3.07 (d, J=12.07 Hz, 2 H), 3.12-3.28 (m, 4 H), 3.39-3.51 (m, 4 H), 3.59-3.72 (m, 2 H), 3.92-4.04 (m, 1 H), 4.15 (s, 2 H), 4.35 (t, J=7.23 Hz, 2 H), 7.09-7.17 (m, 2 H), 7.29 (t, J=6.60 Hz, 1 H), 7.35-7.44 (m, 2 H), 8.13 (s, 1 H), 8.56 (d, J=1.40 Hz, 1 H), 9.80 (br. s., 1 H), 10.31 (t, J=5.83 Hz, 1 H); ES+ MS: 562 (M+H+).

Provenance & Evidence