Diisopropylethylamine → (NZ)-4-acetyl-N-[5-methyl-3-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-ylidene]piperazine-1-carboxamide

Participants

Reaction Steps

In a 20 mL vial were combined a solution of 3-methyl-1-({[(2Z)-5-methyl-3-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2(3H)-ylidene]amino}carbonyl)-1H-imidazol-3-ium iodide (45 mg, 0.09 mmol, Example 18B) dissolved in acetonitrile (0.6 mL) and diisopropylethylamine (21 μL, 0.12 mmol) dissolved in acetonitrile (0.6 mL). Then, to the solution was added 1-(piperazin-1-yl)ethanone (13 mg, 0.1 mmol) dissolved in acetonitrile (0.5 mL). The vial was capped and shaken overnight at room temperature. The reaction was checked by LC/MS and concentrated to dryness. The residue was dissolved in 1:1 DMSO/MeOH and purified by reverse phase HPLC (C18, gradient 10-95% acetonitrile/water/0.1% trifluoroacetic acid) to supply the title compound.

Provenance & Evidence