Hydrochloric Acid → HCID 59321538, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 6-[4-({[5-cyclopropyl-3-(2,6-dichlorophenyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (58 mg, 0.11 mmol) in 2:1 tetrahydrofuran:methanol (1.5 mL) was added 1 N sodium hydroxide (0.18 mL, 0.18 mmol). The solution was heated in a microwave reactor at 120° C. for 500 seconds. The solution was concentrated and water was added followed by 1 N hydrochloric acid (0.18 mL, 0.18 mmol). The solution was extracted twice with ethyl acetate and the combined organic layers were washed with brine and concentrated to afford 6-[4-({[5-cyclopropyl-3-(2,6-dichlorophenyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid (52 mg, 92%). 1H-NMR (400 MHz, DMSO-d6) δ 13.36 (br s, 1H), 8.53 (d, J=9 Hz, 1H), 8.27 (s, 1H), 8.17-8.08 (m, 3H), 7.73 (d, J=9 Hz, 2H), 7.62-7.51 (m, 3H), 6.95 (d, J=9 Hz, 2H), 4.93 (s, 2H), 2.49-2.43 (m, 1H), 1.20-1.10 (m, 4H). HRMS (ESI) C29H20Cl2N2O4 calculated: 531.0873 [M+H]+, found: 531.0873 [M+H]+.

Provenance & Evidence