Ammonia → HCID 58168987, compound

Participants

Reaction Steps

To a mixture of 1-{[2-(adamantan-1-ylamino)-4-(trifluoromethyl)pyrimidin-5-yl]carbonyl}piperidine-4-carboxylic acid (100 mg) and N,N-dimethyl formamide (2 mL) were added 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HBTU) (84 mg) and N,N-diisopropyl ethylamine (77 μL) at room temperature, followed by stirring at the same temperature for 1.5 hours. To the reaction mixture was added 28% aqueous ammonia (2 mL) at room temperature, followed by stirring at the same temperature for 3 hours. To the reaction mixture was added water and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: chloroform-methanol), and the obtained crude product was solidified from a mixed solvent of ethanol and water to obtain 1-{[2-(adamantan-1-ylamino)-4-(trifluoromethyl)pyrimidin-5-yl]carbonyl}piperidine-4-carboxamide (68 mg) as a white powder.

Provenance & Evidence