Reaction Steps
To a solution of (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 (50 mg, 0.078 mmol), ammonium chloride (62.6 mg, 1.171 mmol), and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (44.5 mg, 0.117 mmol) in DMF (781 μL) was added diisopropylethylamine (40.9 μl, 0.234 mmol), and the reaction was heated at 50° C. for 16 h. The reaction mixture was then diluted with DMSO (1 mL), barrier filtered, and purified by reverse-phase HPLC (C18 column, water-acetonitrile, TFA modifier) to give (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-carboxamide, trifluoroacetate salt (27.4 mg, 0.043 mmol, 43% yield) as a yellow solid. MS ESI calcd for C26H22F3N5O2S [M+H]+ 526, found 526. 1H NMR (500 MHz, DMSO) δ 10.21 (s, 1H), 8.64 (s, 1H), 8.48 (s, 1H), 8.22 (s, 1H), 7.88 (s, 1H), 7.64 (s, 1H), 7.57 (s, 1H), 7.35 (s, 1H), 7.28 (s, 1H), 7.25 (d, J=8.2 Hz, 1H), 7.21 (d, J=4.5 Hz, 1H), 7.11 (s, 1H), 2.89-2.80 (m, 2H), 2.39-2.32 (m, 1H), 2.30 (s, 3H), 2.15-2.07 (m, 1H), 2.04-1.89 (m, 2H) ppm.
