Hydrochloric Acid → HCID 59321507, compound

Participants

Reaction Steps

A solution of methyl 6-[4-({[3-(2,4-dichloro-3-pyridinyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (85 mg, 0.16 mmol) (from multiple batches) in THF (1.6 mL) was stirred as a 1 N aqueous sodium hydroxide solution (0.24 mL, 0.24 mmol) was added. The solution was allowed to stir at room temperature overnight. The solution was neutralized with 1 N HCl and concentrated. The residue was partitioned between ethyl acetate and brine. The organic layer was dried with MgSO4. The MgSO4 was slurried in dichloromethane, filtered and the combined filtrates were concentrated to yield 6-[4-({[3-(2,4-dichloro-3-pyridinyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid as a bright yellow foam (66 mg, 76% 0.12 ethyl acetate). 1H NMR (400 MHz, DMSO-d6): δ 13.37 (s, 1H), 8.54-8.51 (m, 2H), 8.28 (d, J=1 Hz, 1H), 8.17-8.08 (m, 3H), 7.80 (d, J=5 Hz, 1H), 7.74 (d, J=9 Hz, 2H), 6.92 (d, J=9 Hz, 2H), 4.96 (s, 2H), 3.49 (septet, J=7 Hz, 1H), 1.34 (d, J=7 Hz, 6H). HRMS C28H21N3O4Cl2 m/z 534.0982, (M+H)+Cal; 534.0980 (M+H)+Obs.

Provenance & Evidence