Ethanol → HCID 66990798, compound

Participants

Reaction Conditions

Reaction Steps

Into a sealable tube, (3S,6R)-1-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-6-methyl-N-[(1S)-1-phenylethyl]-3-piperidinecarboxamide (186 mg, 0.406 mmol), EtOH (5 mL), Hunig's base (0.071 ml, 0.406 mmol), and hydrazine anhydrous (0.076 mL, 2.434 mmol) were added, and the yellow suspension mixture was heated overnight at 110° C. in an oil bath. When the temperature of the reaction reached to 100° C., the solid in the mixture was all dissolved. After overnight, there was a yellow solution as well as a little amount of black colored solid formed. LCMS showed mainly product. CH3OH (5 mL) was added to the solution. The black solid was filtered from the yellow solution. Water (20 mL) was added to the yellow solution, and a solid was formed. The solid was filtered, washed by water, and dried in vacuum. The solid was recrystallized from CH3CN, and the solid was filtered, washed by CH3CN, and dried in vacuum to afford the title compound (120 mg) as a light yellow solid. LC-MS (ES) m/z=471 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.14 (d, J=6.8 Hz, 3H), 1.36 (d, J=7.1 Hz, 3H), 1.66 (m, 1H), 1.68 (m, 1H), 1.77 (m, 2H), 2.34 (m, 1H), 4.94 (m, 1H), 5.38 (s, 2H), 6.07 (s, 2H), 6.56 (s, 1H), 7.19-7.30 (m, 1H), 7.36 (m, 4H), 7.56 (dd, J=8.6, 1.5 Hz, 1H), 7.70 (d, J=8.34 Hz, 1H), 7.94 (s, 1H), 8.39 (d, J=8.1 Hz, 1H), 11.50 (s, 1H).

Provenance & Evidence