Hydrochloric Acid → (Rac)-3-fluoro-5-hydroxy-5-[5-(4-methyl-6-{[4-(trifluoromethyl)pyridin-2-yl]amino}pyridin-2-yl)-1,3-thiazol-2-yl]-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

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Reaction Steps

To a solution of methyl 3-fluoro-5-hydroxy-5-[5-(4-methyl-6-{[4-(trifluoromethyl)pyridin-2-yl]amino}pyridin-2-yl)-1,3-thiazol-2-yl]-5,6,7,8-tetrahydronaphthalene-2-carboxylate, trifluoroacetate salt (200 mg, 0.297 mmol) in tetrahydrofuran (1.2 mL) under argon was added potassium hydroxide (40% aqueous solution, 834 μl, 5.95 mmol), and the reaction was stirred at rt for 16 h. The pH was adjusted to 5 by the addition of aqueous HCl (2.0 M). The resulting mixture was extracted with ethyl acetate (3 times), and the combined organic phases were dried (Na2SO4) and concentrated under reduced pressure to afford (rac)-3-fluoro-5-hydroxy-5-[5-(4-methyl-6-{[4-(trifluoromethyl)pyridin-2-yl]amino}pyridin-2-yl)-1,3-thiazol-2-yl]-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid (115.0 mg, 0.211 mmol, 71% yield) as a light yellow solid. MS ESI calcd for C26H20F4N4O3S [M+H]+ 545, found 545.

Provenance & Evidence