Example 14
A mixture of tert-butyl ((3R,5S)-1-(5-(2-chloropyrimidine-4-carboxamido)-2-methylbenzo[d]thiazol-4-yl)-5-(hydroxymethyl)pyrrolidin-3-yl)carbamate (Intermediate 13, 76 mg, 0.146 mmol), (2-cyano-6-methoxyphenyl)boronic acid (15.55 mg, 0.088 mmol), XPhos Pd G2 (57.6 mg, 0.073 mmol), potassium phosphate tribasic (62.2 mg, 0.293 mmol), 1,4-dioxane (1 mL), and water (0.2 mL) was purged under nitrogen and stirred at 80° C. for 2 hrs. After cooling to r.t., the reaction mixture was concentrated and TFA (1 mL) was added and the resulting mixture was stirred at r.t. for 30 minutes. The reaction mixture was then diluted with acetonitrile and purified with prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% TFA, at flow rate of 60 mL/min). LCMS calculated for C26H28N7O4S (M+H)+: m/z=534.2; Found: 534.2.
