N,N'-Dimethylethylenediamine → HCID 25118690, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(4-iodophenyl)-5-[5-methyl-1-(4-methylbenzyl)-1H-pyrazol-3-yl]-1,2,4-oxadiazole (Example 13, 200 mg, 0.44 mmol), pyrrolidinone (67 μl, 0.88 mmol), potassium phosphate (186 mg, 0.88 mmol), copper(I) iodide (25 mg, 0.13 mmol), N,N′-dimethylethylenediamine (28 μl, 0.26 mmol) and 1,4-dioxane (4 ml) was stirred at 70° C. for 15 h. The reaction mixture was cooled and water (100 mL) and ethyl acetate (100 mL) was added. The layers were separated and the organic layer was washed with water and brine and then dried with magnesium sulfate. The solvent was evaporated and the residue was purified using preparative HPLC, to afford the title compound as a white solid (73 mg, 40%): 1H NMR (400 MHz, CDCl3) 8.21 (d, 2H), 7.79 (d, 2H), 7.13 (d, 2H), 7.08 (d, 2H), 6.79 (s, 1H), 5.41 (s, 2H), 3.93 (t, 2H), 2.65 (t, 2H), 2.33 (s, 3H), 2.26 (s, 3H), 2.20 (quint, 2H); ES-MS m/z 414 (MH)+, HPLC RT (Method E) 4.82 min.

Provenance & Evidence