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

Participants

Reaction Conditions

Reaction Steps

Into a microwave tube, (3S,6R)-1-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-6-methyl-N-(phenylmethyl)-3-piperidinecarboxamide (201 mg, 0.472 mmol), 5 mL of EtOH, Hunig's base (0.330 ml, 1.890 mmol), and hydrazine anhydrous (0.089 mL, 2.83 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, washed by water, and dried in vacuum. The solid was recrystallized using CH3CN, and the solid in the solvent was filtered, washed by EtOAc and CH3CN, and dried in vacuum to afford the title compound (81 mg) as a light yellow solid. LC-MS (ES) m/z=457 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.12-1.21 (m, 3H), 1.59-1.92 (m, 5H), 2.27-2.44 (m, 1H), 2.96 (m, 1H), 4.16-4.45 (m, 2H), 5.38 (s, 2H), 6.00-6.16 (m, 2H), 6.59 (s, 1H), 7.18-7.42 (m, 5H), 7.58 (dd, J=8.6, 1.3 Hz, 1H), 7.71 (d, J=8.6 Hz, 1H), 7.90-8.00 (m, 1H), 8.43-8.55 (m, 1H), 11.50 (s, 1H).

Provenance & Evidence