Sodium Iodide → 2,2-dimethylmalonic acid 5-{(4-{amino[2,2-dimethylpropoxycarbonylimino]methyl}phenylamino)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}-2-pyrimidin-2-yl-2H-[1,2,4]triazol-3-yloxymethyl ester cyclohexyl ester

Participants

Reaction Steps

To a mixture of [1-amino-1-[4-({(5-chloromethoxy-1-pyrimidin-2-yl-1H-[1,2,4]triazol-3-yl)-[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]methyl}amino)phenyl]methylidene]carbamic acid 2,2-dimethylpropyl ester (Example 2b, 80 mg) and DMF (5 mL), sodium iodide (183 mg), potassium hydrogen carbonate (85.5 mg), and 2,2-dimethylmalonic acid monocyclohexyl ester (261 mg) were added, and the resulting mixture was stirred at room temperature for 3 days. Ethyl acetate (30 mL) and water (10 mL) were added to the mixture, and the resulting mixture was shaken, after which the organic layer was collected. Ethyl acetate (20 mL) was added to the aqueous layer, and the resulting mixture was shaken, after which the organic layer was collected. All the organic layers were combined, washed with saturated aqueous sodium chloride solution (10 mL), and dried over anhydrous magnesium sulfate. The resulting mixture was filtered, and the filtrate obtained was concentrated under reduced pressure. The residue obtained was purified by NAM silica gel column chromatography (mixed solvent of heptane-ethyl acetate) to obtain the captioned compound (97.9 mg).

Provenance & Evidence