Dimethylamine → N-(1-((1,5-dimethyl-1H-pyrazol-3-yl)methyl)-3-ethyl-1H-indazol-4-yl)-7-(5-((dimethylamino)methyl)furan-2-yl)imidazo[1,2-a]pyridine-3-carboxamide

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A solution of N-(1-((1,5-dimethyl-1H-pyrazol-3-yl)methyl)-3-ethyl-1H-indazol-4-yl)-7-(5-formylfuran-2-yl)imidazo[1,2-a]pyridine-3-carboxamide (36 mg) in 1 mL of a 1:1 DCM:THF mixture was treated at ambient temperature with excess 2.0 M dimethylamine solution in MeOH. The reaction mixture was stirred at ambient temperature for 30 minutes. A large excess of sodium triacetoxyborohydride (10 equivalents) was added, and the reaction stirred at ambient temperature for 4 hours. The reaction mixture was concentrated under reduced pressure, dissolved in a small amount of MeOH, and subjected to preparative thin-layer chromatography with a 2% 7N ammonia-MeOH, 8% MeOH in DCM solution as eluent to give the desired product (12.8 mg). MS (ES+APCI) m/z=537 (M+H) detected.

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