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

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 6-[4-({[3-{[(2,6-dimethylphenyl)oxy]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (23 mg, 0.043 mmol) in 2:1 tetrahydrofuran:methanol (0.75 mL) was added 1 N sodium hydroxide (0.064 mL, 0.064 mmol). The solution was heated in a microwave reactor at 120° C. for 500 seconds. The mixture was concentrated and water was added followed by 1 N hydrochloric acid (0.064 mL, 0.064 mmol). The mixture was extracted with ethyl acetate and the combined organic layers were washed with brine and concentrated to afford of 6-[4-({[3-{[(2,6-dimethylphenyl)oxy]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid as a yellow solid (14 mg, 62%). 1H-NMR (400 MHz, CDCl3) δ 8.43 (d, J=9 Hz, 1H), 8.29 (d, J=8 Hz, 1H), 8.21 (d, J=9 Hz, 1H), 8.07 (m, 2H), 7.70 (d, J=9 Hz, 2H), 7.10 (d, J=9 Hz, 2H), 7.01-6.62 (m, 3H), 5.06 (s, 2H), 4.97 (s, 2H), 3.30 (septet, J=7 Hz, 1H), 2.23 (s, 6H), 1.39 (d, J=7 Hz, 6H). HRMS (ESI) C32H30N2O5 calculated: 437.2263 (M+H)+, found: 437.2263 (M+H)+.

Provenance & Evidence