Hydrazine → HCID 58504557, compound

Participants

Reaction Conditions

Reaction Steps

Into a microwave tube, (3S)-1-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-N-(1-methyl-1H-pyrazol-5-yl)-3-piperidinecarboxamide (180 mg, 0.428 mmol), 3 mL of EtOH, Hunig's base (0.30 mL, 1.71 mmol), and hydrazine anhydrous (0.081 mL, 2.57 mmol) were added, and the yellow mixture was heated overnight at 110° C. in an oil bath. The solution turned black. LCMS showed mainly product. The black solids were filtered and the yellow filtrate was evaporated. The resulting yellow residue was treated with EtOAc (3 mL) at 50° C. with stirring, and the clear layer of EtOAc solution was poured out. The solid layer was then treated with water (3 mL) at 50° C. with stirring, and the suspension was filtered. The light yellow colored solid was washed by water, and dried to give the title compound (82 mg) as a light yellow solid. LC-MS (ES) m/z=433 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.39-1.57 (m, 1H), 1.62-1.84 (m, 2H), 2.04 (m, 1H), 2.55-2.71 (m, 1H), 2.81-2.94 (m, 1H), 2.97-3.11 (m, 1H), 3.67 (s, 3H), 4.39-4.73 (m, 2H), 5.38 (s, 2H), 6.11 (s, 2H), 6.21 (s, 1H), 6.69 (s, 1H), 7.33 (s, 1H), 7.56-7.77 (m, 2H), 7.97 (s, 1H), 10.00 (s, 1H), 11.50 (s, 1H).

Provenance & Evidence