Acetic Acid → 2-((3-(2-Oxa-6-azaspiro[3.5]nonan-6-ylmethyl)-2-chloro-5-cyanophenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

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Reaction Steps

A suspension of 2-((2-chloro-5-cyano-3-formylphenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (Example 400) (20 mg, 0.053 mmol), acetic acid (9.07 tli, 0.158 mmol) and 2-oxa-6-azaspiro[3.5]nonane (16.79 mg, 0.132 mmol) in THF (0.5 ml) was stirred at room temperature to for 5 min. to achieve solution. DCE (0.5 mL) was added and after 25 min, sodium triacetoxyborohydride (33.6 mg, 0.158 mmol) was added. LCMS analysis found the desired mass of the product. The mixture was stirred overnight. The reaction mixture was then quenched with saturated aqueous NaHCO3 and stirred for 10 minutes. It was dried with a stream of nitrogen and then dissolved in DMF (1.5 mL) and purified by reverse-phase preparative LCMS.

Provenance & Evidence