Hydrochloric Acid → HCID 58456405, compound

Participants

Reaction Steps

To a stirred solution of 8-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]-1,4-dioxaspiro[4.5]decan-8-ol (Example 4B-15, 785 mg, 1.59 mmol) in THF (6 mL) was added HCl (6 M, 5.3 mL, 32 mmol) and the reaction was left to stir for 6 h. The mixture was brought to pH 8 with saturated aqueous sodium bicarbonate, extracted with ethyl acetate (×3), and the combined organic portion was washed with saturated aqueous sodium bicarbonate. The solution was dried over Na2SO4, filtered, concentrated, and purified by flash chromatography to afford 4-hydroxy-4-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]cyclohexanone (625 mg, 1.39 mmol) as a white foam. APCI: [M+H]+ m/z 449.1. 1H NMR (600 MHz, CDCl3) δ 8.64 (d, J=4.9, 1H), 7.90 (s, 1H), 7.86 (s, 1H), 7.46 (s, 1H), 7.26 (s, 1H), 7.06 (s, 1H), 7.04 (d, J=4.9, 1H), 2.92-2.82 (m, 2H), 2.49-2.29 (m, 6H), 2.38 (s, 3H). rhSYK activity=+++

Provenance & Evidence