Potassium Hydroxide → 6-(Methylsulfonyl)-3-{[4-(1-pyrrolidinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

Participants

Reaction Conditions

Reaction Steps

Potassium hydroxide (0.551 g, 9.82 mmol) was added to an orange suspension of methyl 6-(methylsulfonyl)-3-{[4-(1-pyrrolidinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (1.13 g, 1.963 mmol) in methanol (19.63 mL) and water (6.54 mL). The mixture was heated to 65° C. Additional methanol (10 mL) was added, and the mixture was heated overnight for 22 h. The mixture was cooled to room temperature, and the solvent was removed under reduced pressure. The mixture was acidified to pH 4-5 with 2N HCl. The solid was collected by filtration and dried to give 6-(methylsulfonyl)-3-{[4-(1-pyrrolidinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (0.700 g). The filtrate was concentrated to a volume of approximately 3 mL, and the solid precipitate was collected by filtration to afford additional 6-(methylsulfonyl)-3-{[4-(1-pyrrolidinyl)-1-piperidinyl]methyl}-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (0.153 g; 0.853 g total, 73% combined yield). MS (m/z) 562.2 (M+H+).

Provenance & Evidence