Ethanol → HCID 58504431, compound

Participants

Reaction Conditions

Reaction Steps

Into a microwave tube, (3S,6R)-1-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-6-methyl-N-(4-methylcyclohexyl)-3-piperidinecarboxamide (192.2 mg, 0.427 mmol), 5 mL of EtOH, Hunig's base (0.298 mL, 1.706 mmol), and hydrazine anhydrous (0.080 mL, 2.56 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 100° C., the solid in the mixture was all dissolved. After overnight, there was a yellow suspension as well as some black colored solid formed. LCMS showed mainly product. CH3OH (5 mL) was added to the solution. The black solid and the yellow solution were carefully separated due to the black solid being heavier than the yellow solution. Water (20 mL) was added to the yellow solution, and a solid formed. The solid was filtered, washed by water, and dried in vacuum. The solid was recrystallized using CH3CN, and the solid in the solvent was filtered, washed by EtOAc and CH3CN, and dried in vacuum. The yellow residue was dissolved in CH3OH, and purified by HPLC to afford the light yellow title compound (95 mg). LC-MS (ES) m/z=509 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 0.81-1.04 (m, 4H), 1.08-1.37 (m, 6H), 1.40-1.86 (m, 10H), 2.16-2.44 (m, 1H), 2.92 (m, 1H), 3.78 (m, 1H), 5.38 (s, 2H), 6.08 (s, 2H), 6.56 (s, 1H), 7.57 (d, J=8.6 Hz, 1H), 7.67-7.82 (m, 2H), 7.88-7.99 (m, 1H), 8.16 (s, 1H).

Provenance & Evidence