Potassium Hydroxide → 6-[(1-Methylethyl)sulfonyl]-7-(methyloxy)-3-{[4-(4-morpholinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

Participants

Reaction Steps

Potassium hydroxide (0.665 g, 11.85 mmol) was added to a solution of methyl 6-[(1-methylethyl)sulfonyl]-7-(methyloxy)-3-{[4-(4-morpholinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (0.77 g, 1.185 mmol) in methanol (60 mL) and water (20 mL). The reaction mixture was heated to reflux overnight, cooled to room temperature, and diluted with water. The methanol was removed under reduced pressure, and the residue was acidified to about pH 6 with 2N HCl and extracted with methylene chloride (three times). The combined organic extracts were washed twice with brine, dried over Na2SO4, filtered, and concentrated to afford 6-[(1-methylethyl)sulfonyl]-7-(methyloxy)-3-{[4-(4-morpholinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (0.67 g, 89% yield). 1H NMR (400 MHz, DMSO-d6) δ8.81 (s, 1H), 8.03 (s, 1H), 7.91 (t, J=6.53 Hz, 2H), 7.76-7.82 (m, 1H), 7.70 (s, 1H), 4.05-4.12 (m, 5H), 3.81 (dt, J=6.87, 13.61 Hz, 1H), 3.57 (br. s., 4H), 3.01 (d, J=9.79 Hz, 2H), 2.41-2.49 (m, 4H), 2.31-2.40 (m, 1H), 1.78 (d, J=11.54 Hz, 2H), 1.24-1.41 (m, 4H), 1.22 (s, 3H), 1.20 (s, 3H); MS (m/z) 636.2 (M+H+).

Provenance & Evidence