(R)-2-chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazole → (S)-1-(2-chloro-4-nitroimidazol-1-yl)-2-methyl-3-{4-[(4-trifluoromethylbenzylidene)amino]piperazin-1-yl}propan-2-ol

Participants

Reaction Conditions

Reaction Steps

A mixture of (R)-2-chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazole prepared in Example 12 (218 mg, 1 mmol), N-(piperazin-1-yl)-N-(4-trifluoromethylbenzylidene)amine (283 mg, 1.1 mmol) and DMF (2 ml) was stirred at 70-80° C. for 7 hours. The reaction mixture was allowed to return to room temperature and then added water, and the resulting solution was extracted with ethyl acetate twice. The organic phases were combined, washed with water 3 times and a saturated saline solution, dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/acetone=1/1) to afford (S)-1-(2-chloro-4-nitroimidazol-1-yl)-2-methyl-3-{4-[(4-trifluoromethylbenzylidene)amino]piperazin-1-yl}propan-2-ol (402 mg, yield 85%) as a light yellow powder.

Provenance & Evidence