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

Participants

Reaction Steps

To 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 (0.1 g, 0.2 mmol, Example 18B) and pyrrolidine (1.2 equivalents) in anhydrous acetonitrile (3 mL) was added Hunig's base (33 mg, 1.2 equivalents), and the resultant solution was heated at 60° C. for 3 hours. After cooling to room temperature, the reaction mixture was diluted with dichloromethane (25 mL) and washed with water and brine, dried over sodium sulfate, and concentrated under reduced pressure. The crude residue was chromatographed over silica using dichloromethane to give the title compound.

Provenance & Evidence