Hydrazine → (3S)-1-[2-Amino-6-(3-amino-1H-indazol-6-yl)-4-pyrimidinyl]-N-(4-methylphenyl)-3-piperidinecarboxamide

Participants

Reaction Conditions

Reaction Steps

Into a microwave tube, (3S)-1-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-N-(4-methylphenyl)-3-piperidinecarboxamide (90 mg, 0.209 mmol), 3 mL of EtOH, Hunig's base (0.11 mL, 0.627 mmol), and hydrazine anhydrous (0.026 mL, 0.836 mmol) were added, and the resulting yellow mixture was heated at 150° C. for 150 minutes under microwave conditions. The solution turned black. LCMS showed mainly product with 10% of remaining starting material. The black solids were filtered, and the yellow filtrate was evaporated. The resulting yellow residue was dissolved in CH3OH, and purified by HPLC (CH3CN/H2O w/0.1% HCO2H) to afford a formic acid salt of the title compound (31 mg) as a light yellow solid. LC-MS (ES) m/z=443 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.49 (m, 1H), 1.70-1.95 (m, 2H), 1.98-2.12 (m, 1H), 2.25 (s, 3H), 3.16 (m, 1H), 3.48 (m, 1H), 4.49 (m, 2H), 4.74-4.99 (m, 1H), 7.11 (t, J=8.3 Hz, 2H), 7.39 (d, J=7.8 Hz, 1H), 7.49 (d, J=8.3 Hz, 2H), 7.74 (d, J=3.0 Hz, 1H), 7.89 (d, J=10.1 Hz, 1H), 9.97 (d, J=12.4 Hz, 1H), 12.03 (m, 2H).

Provenance & Evidence