Triphosgene → HCID 178522047, compound

Participants

Reaction Steps

4-(2-(2-(1-trityl-1H-imidazol-4-yl)phenoxy)ethyl)aniline (50.0 mg. 0.096 mmol) was dissolved in dichloromethane (DCM, 5 ml) and triethylamine (1 ml), and a solution of triphosgene (0.105 mmol) in DCM (5 ml) was then added to the solution at 0° C. The mixture was stirred at room temperature under N2 for 2 h. Next, tetrahydro-2H-pyran-4-amine (20.0 mg, 0.192 mmol) was added to the reaction solution, and the mixture was stirred at room temperature under N2 for overnight. A saturated aqueous sodium bicarbonate solution was added to the reaction solution, followed by extraction with DCM (3×15 ml). The DCM layer was dried over Na2SO4. The solvent was removed by distillation under the reduced pressure. The residue was dissolved in MeOH/AcOH (4:1, 4 mL) and heated at 80° C. for 2 h. The reaction mixture was basified with aqueous 10% NaOH and the aqueous layer extracted with ethyl acetate (2×30 mL). The combined organic extracts were washed with brine (15 mL), dried over Na2SO4 and concentrated. The residue was purified by flash column chromatography. Yield=78%. 1H NMR (MeOH-d4): 1.40-1.54 (m, 2H), 1.81-1.92 (m, 2H), 3.11-3.15 (m, 2H), 3.46-3.53 (m, 2H), 3.55-3.80 (m, 1H), 3.85-3.95 (m, 2H), 4.35 (t, 2H, J=6.6 Hz), 6.95-7.00 (m, 1H), 7.05-7.13 (m, 2H), 7.19-7.30 (m, 5H), 7.70 (s, 1H), 7.78 (d, 1H, J=7.8 Hz).

Provenance & Evidence