Tetrahydrofuran → (Rac)-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, trifluoroacetate salt

Participants

Reaction Steps

To a solution of (rac)-methyl 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 (250 mg, 0.462 mmol) in THF (1.9 mL) was added potassium hydroxide (40% solution in water, 1.3 mL, 9.25 mmol), and the reaction was stirred at rt for three days. The reaction was diluted with methanol (2 mL) and DMSO (2 mL), barrier filtered, and purified via reverse-phase HPLC (C18 column, water-acetonitrile, TFA modifier) to yield (rac)-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, trifluoroacetate salt as a light brown solid (133.8 mg, 0.209 mmol, 45% yield). MS ESI calcd for C26H21F3N4O3S [M+H]+ 527, found 527. 1H NMR (500 MHz, DMSO) δ 10.21 (s, 1H), 8.63 (s, 1H), 8.48 (d, J=5.1 Hz, 1H), 8.23 (s, 1H), 7.72 (s, 1H), 7.66 (d, J=8.0 Hz, 1H), 7.36 (s, 1H), 7.33 (d, J=8.2 Hz, 1H), 7.21 (d, J=5.1 Hz, 1H), 7.10 (s, 1H), 2.92-2.83 (m, 2H), 2.41-2.33 (m, 1H), 2.31 (s, 3H), 2.16-2.07 (m, 1H), 2.04-1.90 (m, 2H) ppm.

Provenance & Evidence