Hydrochloric Acid → 6-[4-({3-[3-(2,6-Dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]propyl}oxy)phenyl]-2-quinolinecarboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 6-[4-({3-[3-(2,6-dichlorophenyl) -5-(1-methylethyl)-4-isoxazolyl]propyl}oxy)phenyl]-2-quinolinecarboxylate (14 mg, 0.024 mmol) in 1:1 tetrahydrofuran:methanol (1 mL) was added 1 N sodium hydroxide (0.089 mL, 0.089 mmol). The solution was heated in a microwave reactor at 90° C. for 10 minutes. Then 1 N hydrochloric acid (0.089 mL, 0.089 mmol) was added and the mixture was concentrated. Water and ethyl acetate were added to the residue and the layers were separated. The ethyl acetate layer was dried over magnesium sulfate and concentrated to afford 12 mg of 6-[4-({3-[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]propyl}oxy)phenyl]-2-quinolinecarboxylic acid as a yellow solid (0.021 mmol, 89%). 1H-NMR (400 MHz, DMSO-d6) δ 8.42 (d, J=9 Hz, 1H), 8.28 (d, J=9 Hz, 1H), 8.19 (d, J=9 Hz, 1H), 8.06-8.04 (m, 2H), 7.64 (d, J=9 Hz, 2H), 7.41-7.29 (m, 3H), 6.93 (d, J=9 Hz, 2H), 3.90 (t, J=6 Hz, 2H), 3.20 (septet, J=7 Hz, 1H), 2.52 (t, J=6 Hz, 2H), 1.83-1.77 (m, 2H), 1.34 (d, J=7 Hz, 6H). HRMS (ESI) C31H26Cl2N2O4 calculated: 561.1342 (M+H)+, found: 561.1344 (M+H)+.

Provenance & Evidence