Ethanol → (3S,6R)-1-[2-amino-6-(3-amino-1H-indazol-6-yl)-4-pyrimidinyl]-N-cyclopentyl-6-methyl-3-piperidinecarboxamide

Participants

Reaction Conditions

Reaction Steps

Into a microwave tube, (3S,6R)-1-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-N-cyclopentyl-6-methyl-3-piperidinecarboxamide (174 mg, 0.412 mmol), 5 mL of EtOH, Hunig's base (0.288 mL, 1.647 mmol), and hydrazine anhydrous (0.078 mL, 2.471 mmol) were added, and the yellow suspension mixture was heated overnight at 110° C. in an oil bath. LCMS showed mainly product. CH3OH (5 mL) was added to the solution. The black solid and the yellow solution were carefully separated due to the black solid is heavier than yellow solution. Water (20 mL) was added to the yellow solution, and a solid formed. The solid was filtered and washed by water, dried in vacuum, and then treated with EtOAc and CH3OH. The solid in the solvent was filtered, washed by EtOAc, and dried in vacuum to afford the title compound (82 mg) as a light yellow solid. LC-MS (ES) m/z=435 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.14 (m, 3H), 1.65 (m, 12H), 2.14-2.33 (m, 1H), 2.76-3.08 (m, 1H), 3.93-4.12 (m, 1H), 5.38 (s, 2H), 6.07 (s, 2H), 6.57 (s, 1H), 7.57 (m, 1H), 7.69 (m, 1H), 7.87 (m, 1H), 7.94 (s, 1H), 11.49 (s, 1H).

Provenance & Evidence