Dimethylformamide → (S)-N-[4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazin-1-yl]-N-(4-trifluoromethylbenzylidene)amine

Participants

Reaction Steps

To a mixture of (S)-1-(2-chloro-4-nitroimidazol-1-yl)-2-methyl-3-{4-[(4-trifluoromethylbenzylidene)amino]piperazin-1-yl}propan-2-ol prepared in Example 496 (847 mg, 0.85 mmol) and DMF (4 ml), sodium hydride (69 mg, 1.73 mmol) was added followed by stirring for 2.5 hours with cooling on ice-bath. To the reaction mixture, water was added, and the precipitates were filtered off. The resulting solid was washed with methanol and recrystallized from acetone/water to afford (S)-N-[4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazin-1-yl]-N-(4-trifluoromethylbenzylidene)amine (248 mg, yield 69%) as a light yellow powder.

Provenance & Evidence