Ethanol → HCID 58504422, compound

Participants

Reaction Conditions

Reaction Steps

Into a microwave tube, (3S)-1-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-N-[3-(methyloxy)phenyl]-3-piperidinecarboxamide (190 mg, 0.426 mmol), 3 mL of EtOH, Hunig's base (0.223 l, 1.277 mmol), and hydrazine anhydrous (0.053 ml, 1.702 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 off and the yellow filtrate was evaporated. To the resulting brown liquid was added EtOAc (1 mL), and the mixture was warmed to 50° C. Two layers formed. The top layer is EtOAc solution, and it was pipeted to a different vial. The bottom layer is the comparatively pure product. This compound was treated with water at 50° C., and a solid was formed. This material was filtered and dried to give the title compound (90 mg) as a light yellow solid. LC-MS (ES) m/z=459 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.45 (m, 1H), 1.61-1.85 (m, 2H), 2.01 (m, 1H), 2.79-3.06 (m, 2H), 3.74 (s, 3H), 4.36-4.79 (m, 2H), 5.37 (s, 2H), 6.02-6.15 (s, 2H), 6.55-6.74 (m, 2H), 7.09-7.26 (m, 2H), 7.32-7.41 (m, 1H), 7.51-7.78 (m, 2H), 7.91-8.00 (m, 1H), 10.01 (s, 1H), 11.50 (s, 1H).

Provenance & Evidence