Potassium Hydroxide → HCID 67418827, compound

Participants

Reaction Steps

Potassium hydroxide (1.805 g, 32.2 mmol) was added to a solution of methyl 7-(ethyloxy)-6-(ethylsulfonyl)-3-{[4-(4-morpholinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (2.09 g, 3.22 mmol) in methanol (60 mL) and water (20 mL). The mixture was heated to reflux overnight, cooled to room temperature, and diluted with water. The methanol was removed under reduced pressure, and the remaining aqueous solution was acidified to pH 6 and extracted with methylene chloride (three times). The combined organic extracts were washed with brine (two times), dried over Na2SO4, filtered, and concentrated in vacuo to afford 7-(ethyloxy)-6-(ethylsulfonyl)-3-{[4-(4-morpholinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (1.82 g, 89% yield). 1H NMR (400 MHz, DMSO-d6) ™ 8.80 (s, 1H), 8.03 (s, 1H), 7.88-7.94 (m, 2H), 7.76-7.82 (m, 1H), 7.67 (s, 1H), 4.37 (q, J=6.94 Hz, 2H), 4.08 (br. s., 2H), 3.50-3.62 (m, 6H), 2.99 (br. s., 2H), 2.31-2.59 (m, 6H), 1.79 (d, J=12.30 Hz, 2H), 1.45 (t, J=6.90 Hz, 3H), 1.23-1.41 (m, 3H), 1.14 (t, J=7.40 Hz, 3H); MS (m/z) 636.2 (M+H+).

Provenance & Evidence