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

Participants

Reaction Conditions

Reaction Steps

Into a microwave tube, (3S)-1-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-N-(3-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 in microwave. 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 (77 mg) as a light yellow solid. LC-MS (ES) m/z=443 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.52 (m, 1H), 1.84 (m, 2H), 2.07 (m, 1H), 2.27 (s, 3H), 3.50 (m, 1H), 4.48 (m, 2H), 4.75 (m, 1H), 4.90-5.13 (m, 1H), 6.87 (s, 1H), 6.94-7.08 (m, 1H), 7.13-7.26 (m, 1H), 7.41 (m, 6H), 7.75 (s, 1H), 7.83-8.00 (m, 1H), 10.00 (s, 1H), 12.07 (s, 2H).

Provenance & Evidence