Hydrazine → HCID 58504398, compound

Participants

Reaction Conditions

Reaction Steps

Into a microwave tube, (3S)-1-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-N-(4-chlorophenyl)-3-piperidinecarboxamide (190 mg, 0.421 mmol), 3 mL of EtOH, Hunig's base (0.22 mL, 1.26 mmol), and hydrazine anhydrous (0.053 mL, 1.69 mmol) were added, and the yellow mixture was heated at 150° C. for 180 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 at 50° C., EtOAc was used to triturate. When the solution turned slightly cloudy, it was cooled down to room temperature to get pure crystallized light yellow title compound (59 mg). LC-MS (ES) m/z=463 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.45 (m, 1H), 1.64-1.85 (m, 2H), 1.99 (m, 1H), 2.55 (m, 1H), 2.78-3.07 (m, 2H), 4.38-4.82 (m, 2H), 5.37 (s, 2H), 6.10 (s, 2H), 6.64-6.74 (m, 1H), 7.31-7.40 (m, 2H), 7.53-7.76 (m, 4H), 7.97 (s, 1H), 10.18 (s, 1H), 11.50 (s, 1H).

Provenance & Evidence