Diisopropylethylamine → HCID 53358061, compound

Participants

Reaction Steps

3,3,3-Trifluoropropanoic acid (0.03 mL, 0.29 mmol), N-[(dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methylmethanaminium hexafluorophosphate (0.12 g, 0.30 mmol) and diisopropylethylamine (0.21 mL, 1.21 mmol) were added to a stirred solution of 3-{4-[(3R)-piperidin-3-ylamino]pyrimidin-2-yl}pyrazolo[1,5-a]pyridine-5-carbonitrile (Preparation 7b, 0.11 g, 0.24 mmol) in N,N′-dimethylformamide (3 mL) and the mixture was stirred at room temperature for 20 hours. The reaction mixture was then partitioned between dichloromethane and 4% aqueous sodium hydrogen carbonate solution. The organic layer was separated, washed with 4% aqueous sodium hydrogen carbonate solution, dried (MgSO4) and the solvents were evaporated in vacuo. The crude product was purified by flash chromatography (200:1 to 10:1 chloroform/methanol) to give a residue that was repurified by flash chromatography (1:1 hexane/ethyl acetate to 100% ethyl acetate) to give the title compound (0.02 g, 19%) as a pale yellow solid.

Provenance & Evidence