3-Aminopyridine → HCID 24964058, compound

Participants

Reaction Steps

5-Bromo-2-(3-(piperidin-4-ylidenemethyl)phenoxy)pyrimidine trifluoroacetate (0.315 mmol, from Step 5), in acetonitrile (1.5 mL) was treated with phenyl pyridin-3-ylcarbamate (75 mg, 0.35 mmol, prepared according to the procedure described in Synthesis, 1997, 1189-1194 from 3-aminopyridine) and diisopropylethylamine (0.192 mL, 1.10 mmol) and stirred at room temperature. After 72 h, the reaction was concentrated and the residue was purified by flash chromatography on silica gel (0-10% ethanol (containing 11% aq NH4OH):dichloromethane) to afford the title compound (0.114 g, 78% yield) as a white foam. MS (APCI) M+1=466; 1H NMR (400 MHz, CDCl3) δ ppm 2.48 (t, J=5.36 Hz, 2H) 2.61 (t, J=5.36 Hz, 2H) 3.55-3.63 (m, 2H) 3.66-3.73 (m, 2H) 6.41 (s, 1H) 7.01-7.09 (m, 2H) 7.12 (d, J=7.80 Hz, 1H) 7.40 (t, J=7.80 Hz, 1H) 7.43-7.48 (m, 1H) 7.89 (br. s., 1H) 8.21 (d, J=4.29 Hz, 1H) 8.48 (d, J=8.97 Hz, 1H) 8.58 (s, 2H) 8.88 (br. s, 1H).

Provenance & Evidence