Cyanoacetic acid → 3-(9-((5-chloro-2-((1-(2-hydroxyethyl)-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)-3-azaspiro[5.5]undecan-3-yl)-3-oxopropanenitrile

Participants

Reaction Steps

To a solution of 2-[4-[[4-(3-azaspiro[5.5]undecan-9-ylamino)-5-chloropyrimidin-2-yl]amino]-1H-pyrazol-1-yl]ethanol (200.5 mg, 0.4940 mmol) in a mixture of dichloromethane (40 mL) and DMF (10 mL) were added 2-cyanoacetic acid (46.5 mg, 0.547 mmol), HATU (375.2 mg, 0.9868 mmol) and TEA (100.5 mg, 0.9932 mmol). The mixture was stirred at room temperature for 2 h. The mixture was diluted with water (50 mL), and extracted with DCM/MeOH (10/1, 50 mL×3). The combined organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=100/1 to 10/1) to give the product as a yellow solid (105 mg, 44.94%).

Provenance & Evidence