Triethylamine → HCID 86268829, compound

Participants

Reaction Steps

A mixture of Example A4 (0.20 g, 0.67 mmol) in DCM (4 mL) was cooled in an ice-water bath and treated with trimethylacetyl chloride (0.16 g, 1.35 mmol). The mixture was allowed to warm up to RT and stirred for 30 min. The reaction mixture was cooled to 0° C. and then diluted with DCM (4 mL). Triethylamine (0.5 mL, 3.61 mmol) was added and then a solution of triphosgene (80 mg, 0.26 mmol) in DCM (4 mL) was added drop-by-drop under the same conditions. The reaction mixture was allowed to warm to RT and stirred at RT overnight. The mixture was quenched with NaHCO3 solution and extracted with DCM (2×). The organic was dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified via silica gel chromatography (EtOAc) to obtain 5-(tert-butyl)-3-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)-1,3,4-oxadiazol-2(3H)-one (114 mg, 37.8%). 1H NMR (400 MHz, DMSO-d6): δ 8.39 (d, J=5.7 Hz, 1H), 8.27 (s, 1H), 7.97 (s, 1H), 7.78 (d, J=8.7 Hz, 1H), 7.70 (d, J=8.8 Hz, 1H), 7.23 (d, J=2.4 Hz, 1H), 6.67 (dd, J=5.7, 2.4 Hz, 1H), 3.85 (s, 3H), 2.37 (s, 3H), 1.33 (s, 9H); MS (ESI) m/z: 407.2 (M+H+).

Provenance & Evidence