Trifluoroacetic acid → HCID 178424320, compound

Participants

Reaction Steps

6-(2-Methylcyclohexylamino)-5-nitropyridin-2-ol (100 mg, 0.398 mmol) and nickel (11.68 mg, 0.199 mmol) in MeOH (10 mL) were stirred at 22° C. for 24 hr under H2. After filtration through Celite®, the solution was concentrated in the presence of a few drops of TFA. The residue was dissolved in trimethoxymethane (2112 mg, 19.90 mmol) and stirred overnight with a drop of TFA. The mixture was concentrated. The residue was diluted with water, neutralized with NaHCO3 solution and extracted with EtOAC. The EtOAc extract was concentrated and the residue was purified by column chromatography to give the title compound as a brown oil (37 mg). LCMS m/z=232.10 [M+H]+, 1H NMR (400 MHz, CDCl3) major isomer; δ ppm 0.75 (d, J=6.3 Hz, 3H), 1.22-2.20 (m, 9H), 4.18-4.27 (m, 1H), 6.89 (d, J=8.9 Hz, 1H), 8.17 (d, J=8.9 Hz, 1H), 8.52 (s, 1H).

Provenance & Evidence