Methanesulfonyl chloride → HCID 69482763, compound

Participants

Reaction Steps

A solution of 1-(2-aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-N-(tetrahydro-2-furanylmethyl)-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 1.44-1.67 (m, 1 H), 1.80-1.89 (m, 3 H), 2.90 (s, 3 H), 3.19-3.29 (m, 2 H), 3.34-3.41 (m, 1 H), 3.53-3.61 (m, 1 H), 3.64-3.71 (m, 1 H), 3.77-3.87 (m, 1 H), 3.97-4.08 (m, 1 H), 4.14 (s, 2 H), 4.35 (t, J=6.18 Hz, 2 H), 7.10-7.18 (m, 2 H), 7.26 (t, J=5.76 Hz, 1 H), 7.40 (dd, J=8.14, 5.48 Hz, 2 H), 8.11 (s, 1 H), 8.55 (s, 1 H), 10.39 (t, J=5.97 Hz, 1 H), 17.10 (s, 1 H); ES+ MS: 519 (M+H+).

Provenance & Evidence