Ethyl Acetate → HCID 66990901, compound

Participants

Reaction Conditions

Reaction Steps

To cis-1-[6-(4-cyano-3-fluorophenyl)-2-(methylamino)-4-pyrimidinyl]-N-cyclohexyl-6-(trifluoromethyl)-3-piperidinecarboxamide (152 mg, 0.301 mmol) in ethanol (6 mL) was added hydrazine monohydrate (0.4 mL, 8.16 mmol), and the reaction mixture was stirred overnight at 100° C. into a sealed tube. The reaction was allowed to cool to room temperature and poured onto water and EtOAc. The organic layer was separated, and the aqueous layer was further extracted with EtOAc. The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated. Flash chromatography on SiO2 (gradient: 100% CH2Cl2 to 90:10:1 CH2Cl2:CH3OH:NH4OH) afforded the title compound (116 mg) as an off-white solid. LC-MS (ES) m/z=517 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.05-1.34 (m, 5H), 1.56 (m, 1H), 1.62-1.85 (m, 7H), 2.08. (m, 1H), 2.34 (m, 1H), 2.84 (s, 3H), 3.07 (bs, 1H), 3.53 (m, 1H), 5.39 (s, 2H), 6.73 (bs, 1H), 6.78 (s, 1H), 7.63-7.69 (m, 1H), 7.70-7.75 (m, 1H), 7.84 (d, J=7.8 Hz, 1H), 8.02 (bs, 1H), 11.52 (s, 1H).

Provenance & Evidence