Trifluoroacetic acid → HCID 178515773, compound

Participants

Reaction Steps

5-Nitro-6-(tetrahydro-2H-pyran-4-ylamino)pyridin-2-ol (0.173 g, 0.723 mmol) and methanol (160 mL) were stirred at 25° C. for 4 h with excess Raney nickel and under an atmosphere of hydrogen. After 4 h the solution was filtered by vacuum filtration through Celite® and the solvent was removed under reduced pressure. The intermediate 5-amino-6-(tetrahydro-2H-pyran-4-ylamino)pyridin-2-ol was then taken up in trimethyl orthoformate (20.0 mL, 183 mmol), and trifluoroacetic acid (0.05 ml, 0.649 mmol) was added. The solution was stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue was purified by preparative HPLC to give the title compound (0.0246 g). LCMS m/z=220.0 [M+H]+; 1H NMR (400 MHz, acetonitrile-d3) δ ppm 2.10-2.20 (m, 2H), 2.31 (qd, J1=12.4 Hz, J2=4.7 Hz, 2H), 3.59 (td, J1=12.0 Hz, J2=1.9 Hz, 2H), 4.11 (dd, J1=11.8 Hz, J2=4.5 Hz, 2H), 4.80-4.90 (m, 1H), 6.98 (d, J=8.9 Hz, 1H), 8.18 (d, J=8.9 Hz, 1H), 8.56 (s, 1H).

Provenance & Evidence