Diisopropylethylamine → HCID 117899572, compound

Participants

Reaction Steps

O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (546 mg) was added to a solution of 1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (329 mg) in DMF (10 mL) at room temperature, and the mixture was stirred at the same temperature for 15 minutes. 7-Methyl-4-[6-(piperidin-4-yl methoxy)-5-(trifluoromethyl)pyridin-3-yl]-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile monohydrochloride (500 mg) and N,N-diisopropylethylamine (0.38 mL) were added to the reaction mixture at room temperature, and the mixture was stirred at the same temperature overnight. After EtOAc and a saturated aqueous NaHCO3 solution were added to the reaction mixture, extraction thereof was performed using EtOAc, and the extract was washed with water and saturated brine. The organic layer was dried over MgSO4 and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (CHCl3:MeOH=100:0 to 96:4), whereby tert-butyl 4-{[4-({[5-(2-cyano-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-3-(trifluoromethyl)pyridin-2-yl]oxy}methyl)piperidin-1-yl]carbonyl}piperidine-1-carboxylate (488 mg) was obtained as a solid.

Provenance & Evidence