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

Participants

Reaction Conditions

Reaction Steps

Into a microwave tube, (3S)-1-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-N-(3,4-difluorophenyl)-3-piperidinecarboxamide (90 mg, 0.199 mmol), 3 mL of EtOH, hunig's base (0.104 ml, 0.597 mmol), and hydrazine anhydrous (0.025 ml, 0.796 mmol) weres added, and the yellow mixture was heated at 150° C. for 150 minutes under microwave conditions. The solution turned black. LCMS showed mainly product. 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 the title compound (65 mg) as a light yellow solid. LC-MS (ES) m/z=465 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.50 (m, 1H), 1.69-1.96 (m, 2H), 2.06 (m, 1H), 3.19 (m, 1H), 3.40-3.55 (m, 1H), 4.36-4.56 (m, 2H), 4.73-4.97 (m, 1H), 6.91-7.09 (m, 1H), 7.25-7.52 (m, 4H), 7.66-8.03 (m, 4H), 10.25-10.42 (m, 1H), 10.33 (d, J=8.8 Hz, 1H), 12.09 (s, 2H).

Provenance & Evidence