Sodium Hydroxide → HCID 44816889, compound

Participants

Reaction Steps

A solution of ethyl 5-fluoro-1-{4-[3-(hydroxymethyl)-1H-pyrazol-1-yl]benzyl}-4-oxo-1,4-dihydroquinoline-3-carboxylate (0.050 g, 0.119 mmol) in 2 mL of tetrahydrofuran was cooled to −40° C. under nitrogen, and [bis(2-methoxyethyl)-amino]sulfur trifluoride (0.029 g, 0.13 mmol) was added. The reaction mixture was warmed to room temperature and after 4 hours 1 N NaOH (0.50 mL, 0.50 mmol) was added. After 30 minutes, the tetrahydrofuran was removed in vacuo, and 1 mL DMSO and 0.5 mL 40% NaOH were added. After 3 hours, the reaction mixture was acidified with 6 N HCl to pH ˜2, filtered, and purified via reverse phase HPLC to provide the title compound which gave a proton NMR spectrum consistent with theory and a mass ion (ES+) of 395.9 for M+H+: 1H NMR (400 MHz, d6-DMSO) δ 9.30 (s, 1H), 8.50 (s, 1H), 7.87-7.80 (m, 3H), 7.66 (d, J=8.8 Hz, 1H), 7.43 (d, J=8.6 Hz, 2H), 7.40-7.35 (m, 1H), 6.67 (s, 1H), 6.52 (s, 1H), 5.88 (s, 2H), 5.62 (d, J=10.2 Hz, 2H).

Provenance & Evidence