Sodium hydride → (R)-2-methyl-6-nitro-2-{4-[4-(4-trifluoromethoxybenzyl)piperazin-1-yl]phenoxymethyl}-2,3-dihydroimidazo[2,1-b]oxazole

Participants

Reaction Conditions

Reaction Steps

4-[4-(4-Trifluoromethoxybenzyl)piperazin-1-yl]phenol (3.36 g, 9.54 mmol) was dissolved in of DMF (20 ml). To the solution, sodium hydride (420 mg, 10.5 mmol) was added at room temperature, and the solution was stirred for 15 minutes at 80° C. To the reaction mixture, (R)-2-chloro-1-(2-methyloxiran-2-ylmethyl)-4-nitroimidazole prepared in Example 12 (2.18 g, 10.0 mmol) was added with cooling on ice-bath followed by stirring for further 15 minutes at 80° C. To the reaction mixture, ice-water was added, and the solution was stirred vigorously. The precipitates were filtered off, washed with water and dissolved in methylene chloride. The solution was washed with a saturated saline solution, dried over magnesium sulfate and then filtered. The resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1) and then crystallized from methylene chloride-ethyl acetate to afford (R)-2-methyl-6-nitro-2-{4-[4-(4-trifluoromethoxybenzyl)piperazin-1-yl]phenoxymethyl}-2,3-dihydroimidazo[2,1-b]oxazole (2.0 g, yield 40%) as a light yellow powder.

Provenance & Evidence