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

Participants

Reaction Conditions

Reaction Steps

Into a microwave tube, (3S)-1-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-N-(2-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 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 (50 mg) as a light yellow solid. LC-MS (ES) m/z=443 [M+H]+. 1H NMR (400 MHz, CD3OD): δ 1.73 (m, 1H), 1.91-2.15 (m, 2H), 2.26 (m, 4H), 2.70-2.92 (m, 1H), 3.44 (m, 1H), 3.50-3.84 (m, 1H), 4.30 (d, J=12.6 Hz, 1H), 4.67-5.11 (m, 1H), 6.79-6.95 (m, 1H), 7.09-7.33 (m, 4H), 7.47 (d, J=7.8 Hz, 1H), 7.83 (s, 1H) 7.99 (m, 1H).

Provenance & Evidence