Diethyl Ether → N-(3-cyclopropyl-1-((1-ethyl-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 (531 mg, 1.57 mmol) in NMP (6 mL) at 0° C. was added 2,4,6-trichlorobenzoyl chloride (250 μL, 1.56 mmol). The cold bath was removed once the addition was complete. The mixture was stirred for a further 1 hour. 3-Cyclopropyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-amine (310 mg, 1.10 mmol; prepared as in Example 61, step E) was added and the reaction mixture was heated to 88° C. for 11 hours. The mixture was cooled to ambient temperature. Vacuum distillation was set up and NMP was removed until the reaction mixture became a thick oily residue, to which 10% NaOH aqueous solution (10 mL) was added 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 organic extracts were combined, dried (Na2SO4) and concentrated under vacuum to give a residual oil, which was triturates with Et2O (50 mL). The resulting solids were washed with Et2O (40 mL) to give the final product (492 mg). MS (ES+APCI) m/z=596 (M+H).

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