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

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 6-[4-({[3-{[(2,6-dichlorophenyl)thio]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (5 mg, 0.008 mmol) in 1:1 tetrahydrofuran:methanol (0.5 mL) was added 1 N sodium hydroxide (0.04 mL, 0.04 mmol). The solution was heated in a microwave reactor at 90° C. for 10 minutes and 1 N hydrochloric acid (0.04 mL, 0.04 mmol) was added. The mixture was concentrated and the residue was taken up with ethyl acetate and washed with water. The organic layer was dried over magnesium sulfate and concentrated to afford 6-[4-({[3-{[(2,6-dichlorophenyl)thio]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid (5 mg, 100%). 1H-NMR (400 MHz, CDCl3) δ 8.44 (d, J=9 Hz, 1H), 8.29 (d, J=9 Hz, 1H), 8.21 (d, J=9 Hz, 1H), 8.10-8.07 (m, 2H), 7.70 (d, J=9 Hz, 2H), 7.34-7.14 (m, 3H), 7.10 (d, J=9 Hz, 2H), 5.08 (s, 2H), 4.16 (s, 2H), 3.20 (septet, J=7 Hz, 1H), 1.32 (d, J=7 Hz, 6H). HRMS (ESI) C30H24Cl2N2O4S calculated: 579.0912 (M+H)+, found: 579.0925 (M+H)+.

Provenance & Evidence