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

Participants

Reaction Steps

Potassium hydroxide (1.36 g, 2.42 mmol) was added to a solution of methyl 7-(ethyloxy)-6-(methylsulfonyl)-3-{[4-(4-morpholinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (1.54 g, 2.423 mmol) in methanol (60 mL) and water (20 mL). The reaction mixture was heated to reflux overnight. The mixture was cooled to room temperature, diluted with water, and concentrated in vacuo to remove methanol. The solid precipitate was collected by filtration, washed with cold water, and dried to afford 7-(ethyloxy)-6-(methylsulfonyl)-3-{[4-(4-morpholinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (1.6 g, >99% yield) as the potassium salt. 1H NMR (400 MHz, DMSO-d6) δ 8.14 (s, 1H), 7.92 (d, J=7.53 Hz, 1H), 7.79 (d, J=7.78 Hz, 1H), 7.68 (t, J=7.78 Hz, 1H), 7.52 (s, 1H), 4.34 (q, J=6.94 Hz, 2H), 3.49-3.55 (m, 4H), 3.44 (s, 2H), 3.17 (s, 3H), 2.53 (br. s., 2H), 2.31-2.38 (m, 4H), 1.93-2.02 (m, 1H), 1.85 (t, J=11.29 Hz, 2H), 1.52 (d, J=11.04 Hz, 2H), 1.46 (t, J=7.03 Hz, 3H), 0.94-1.07 (m, 2H); MS (m/z) 622.2 (M+H+).

Provenance & Evidence