Hydrochloric Acid → N-(3-ethyl-1-((1-ethyl-1H-pyrazol-4-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide dihydrochloride

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Reaction Steps

To a solution of N-(1-((1H-pyrazol-4-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (20 mg, 0.052 mmol; prepared according to Example 21, Step A) in dry N,N-dimethyl formamide (0.5 mL) was added cesium hydroxide hydrate (8.7 mg, 0.052 mmol) and bromoethane (5.7 mg, 0.052 mmol). The mixture was stirred under a nitrogen atmosphere for 60 minutes at ambient temperature. The mixture was filtered, washed with methanol and ethyl acetate, and concentrated under a stream of nitrogen. The material was purified using preparative thin layer chromatography on silica, eluting with 10% methanol in dichloromethane. The isolated product was dissolved in a mixture of dichloromethane and methanol. Hydrogen chloride (0.5 mmol; 2M solution in diethyl ether) was added. Removal of the solvent under reduced pressure followed by high vacuum gave N-(3-ethyl-1-((1-ethyl-1H-pyrazol-4-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide dihydrochloride (5.0 mg). MS (APCI), positive scan, m/z=414.2 (M+H).

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