Cyclohexylamine → (3S,6R)-1-[2-Amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-N-cyclohexyl-6-methyl-3-piperidinecarboxamide

Participants

Reaction Steps

To a solution of (3S,6R)-1-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-6-methyl-3-piperidinecarboxylic acid (415 mg, 1.128 mmol) and HATU (533 mg, 1.401 mmol) in DMF (3 mL) into a 10 mL round-bottomed flask was added Hunig's base (0.408 mL, 2.34 mmol), and the resulting mixture was stirred at room temperature for 15 minutes. Cyclohexylamine (0.16 mL, 1.401 mmol) was added, and the reaction mixture was stirred at room temperature for 0.5 hours. LCMS showed reaction was completed. The reaction was poured into water, and EtOAc was added to extract the product. The product stayed in the EtOAc layer. The organic layer solution was concentrated, and the formed solid was recrystallized in CH3CN to afford the title compound (245 mg) as a light yellow solid. LC-MS (ES) m/z=437 [M+H]+.

Provenance & Evidence