Hydrochloric Acid → 6-[4-({[5-Cyclopentyl-3-(2,6-dichlorophenyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 6-[4-({[5-cyclopentyl-3-(2,6-dichlorophenyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (73 mg, 0.13 mmol) in 2:1 tetrahydrofuran:methanol (1.5 mL) was added 1N sodium hydroxide (0.19 mL, 0.19 mmol). A solid was seen to precipitate. The mixture was heated in a microwave reactor at 120° C. for 500 seconds and then was concentrated and the residue was taken up with water and hydrochloric acid (0.19 mL, 0.19 mmol) was added. Ethyl acetate was added and the layers were separated. The aqueous layer was extracted once more with ethyl acetate. The combined organic layers were washed with brine and concentrated to afford 6-[4-({[5-cyclopentyl-3-(2,6-dichlorophenyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid (58 mg, 82%). 1H-NMR (400 MHz, DMSO-d6) δ 13.36 (br s, 1H), 8.53 (d, J=9 Hz, 1H), 8.27 (s, 1H), 8.18-8.08 (m, 3H), 7.73 (d, J=9 Hz, 2H), 7.63-7.51 (m, 3H), 6.92 (d, J=9 Hz, 2H), 4.87 (s, 2H), 3.59-3.51 (m, 1H), 2.11-2.03 (m, 2H), 1.84-1.64 (m, 6H). HRMS (ESI) C31H24Cl2N2O4 calculated: 559.1186 (M+H)+, found: 559.1183 (M+H)+.

Provenance & Evidence