Cesium carbonate → 2-{3-[2-(1-{[(Propan-2-ylideneamino)oxy]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl methanesulphonate

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Reaction Steps

To a solution of acetone oxime (9.3 mg) in N,N-dimethylformamide (0.28 ml) at room temperature was added 3 Å molecular sieve, and the mixture was stirred at this temperature for 2 hours. Thereafter, 2-(3-{2-[1-(chloroacetyl)piperidin-4-yl]-1,3-thiazol-4-yl}-4,5-dihydro-1,2-oxazol-5-yl)phenyl methanesulphonate (50 mg) and caesium carbonate (64 mg) were added thereto, and the mixture was stirred at room temperature for 18 hours. Subsequently, the mixture was filtered and extracted twice with ethyl acetate. The combined organic phases were dried over magnesium sulphate and concentrated. Purification by column chromatography gave 2-{3-[2-(1-{[(propan-2-ylideneamino)oxy]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl methanesulphonate (5 mg, 10%).

Provenance & Evidence