Sodium Hydroxide → N-(3-cyclopropyl-1-((1-isopropyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-yl)-7-(2-(4-isopropylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxamide

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To a solution of lithium 7-(2-(4-isopropylpiperazin-1-yl)ethoxy)imidazo[1,2-a]pyridine-3-carboxylate (123 mg, 0.364 mmol; prepared according to Example 62, Step B) in NMP (10 mL) at 0° C. was added 2,4,6-trichlorobenzoyl chloride (57.9 μL, 0.363 mmol). The cold bath was removed once the addition was complete. The mixture was stirred for one hour. 3-Cyclopropyl-1-((1-isopropyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-amine (80 mg, 0.271 mmol; prepared according to Example 63, step E) was added and the reaction mixture was heated at 88° C. for 11 hours. The reaction mixture was cooled to ambient temperature, and NMP was removed under reduced pressure to give an oily residue. To this was added 10% NaOH aqueous solution (10 mL) and the resulting clear solution was stirred at 80° C. for 30 minutes. The solution was cooled to ambient temperature and extracted with DCM. The combined organic extracts were dried (Na2SO4) and concentrated under reduced pressure to give a residue, which was triturated with Et2O (50 mL). The resulting solids were isolated by filtration, washed with ether and dried under vacuum to give the product (101 mg). MS (ES+APCI) m/z=610 (M+H).

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