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

Participants

Reaction Steps

To a solution of (3S,6R)-1-[2-amino-6-(1H-indazol-6-yl)-4-pyrimidinyl]-6-methyl-3-piperidinecarboxylic acid (95 mg, 0.270 mmol) and HATU (123 mg, 0.324 mmol) in DMF (3 mL) was added Hunig's base (0.094 mL, 0.54 mmol), and the mixture was stirred at room temperature for 15 minutes. Then cyclohexylamine (0.037 mL, 0.324 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 was concentrated to dryness, and the resulting glass like solid was dissolved in CH3OH. Water was poured into the solution, and a white solid was formed, which was filtered, washed by water, and dried under vacuum to give the title compound (100 mg) as a white solid. LC-MS (ES) m/z=434 [M+H]+. 1H NMR (400 MHz, CD3OD): δ 1.29 (m, 9H), 1.62-2.09 (m, 9H), 2.32-2.45 (m, 1H), 3.06-3.18 (m, 1H), 3.61-3.73 (m, 1H), 4.44-4.84 (m, 1H), 6.53 (s, 1H), 7.65 (dd, J=8.5, 1.4 Hz, 1H), 7.85 (dd, J=8.5, 1.4 Hz, 1H), 8.06 (s, 1H), 8.09 (s, 1H).

Provenance & Evidence