Triethylamine → tert-butyl 3-((2-amino-6-((R)-3-(pyrrolidine-1-carbonyl)piperidin-1-yl)pyridin-3-yl)carbamoyl)piperidine-1-carboxylate

Participants

Reaction Steps

To a solution of (R)-(1-(5,6-diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone (3.60 mmol) in 1,4-dioxane (20 mL) was added (R)-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid (3.60 mmol), 1-Propanephosphonic acid cyclic anhydride (10.8 mmol), and triethylamine (32.4 mmol). The reaction mixture was stirred at room temperature for 16 h. The solvent was removed under reduced pressure and a solution of methanol/dichloromethane (1:9, 50 mL) was added followed by a saturated aqueous solution of sodium bicarbonate (50 mL), and the layers were separated. The aqueous layer was extracted again with methanol/dichloromethane (1:9, 25 mL) and the combined organics were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford tert-butyl 3-((2-amino-6-((R)-3-(pyrrolidine-1-carbonyl)piperidin-1-yl)pyridin-3-yl)carbamoyl)piperidine-1-carboxylate which was used without further purification.

Provenance & Evidence