Hydrochloric Acid → HCID 118092616, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydroxide (1 M in water, 1.41 mL, 1.41 mmol) was added to a solution of ethyl-4-{[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]oxy}benzoate (349 mg, 0.706 mmol) in methanol (3.53 mL) and stirred at 60° C. for 16 hours. THF (5 mL) was added to the reaction mixture and heated at 60° C. for 6 hours. The reaction was cooled to room temperature and acidified with aqueous 1N HCl. The aqueous layer was extracted with 3:1 CHCl3:isopropanol (3×). The combined organic layers were dried with magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (MeOH/DCM) to afford 4-{[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]oxy}benzoic acid (114 mg, 0.244 mmol) as a white solid. MS ESI calc'd for C24H18F3N4O3 [M+H]+ 467. found 467.

Provenance & Evidence