Methyl iodide → HCID 66778146, compound

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Reaction Steps

To a solution of ethyl 3-[{[4-({cyclohexyl[3-ethyl-1-(3-methoxyphenyl)-1H-pyrazol-4-yl]methyl}amino)phenyl]carbonyl}(methyl)amino]propanoate (1.1 g) synthesized in Example 78(4) in N,N-dimethylacetamide (5 mL) was added sodium hydride (0.16 g) under ice-cooling and, after stirring for 30 min, methyl iodide (0.37 mL) was added. The ice bath was removed, the reaction mixture was stirred at room temperature overnight, saturated aqueous ammonium chloride solution was added and the mixture was extracted with diethyl ether. The extract was washed with brine to give ethyl 3-[({4-[{cyclohexyl[3-ethyl-1-(3-methoxyphenyl)-1H-pyrazol-4-yl]methyl}(methyl)amino]phenyl}carbonyl)(methyl)amino]propanoate (0.23 g, 75%) as a pale-yellow oil. This was dissolved in ethanol (3.0 mL), 1N aqueous sodium hydroxide solution (1.5 mL) was added at room temperature, and the mixture was stirred at room temperature for 0.5 hr. Ethanol was evaporated under reduced pressure, 1N hydrochloric acid (1.5 mL) was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:1, volume ratio) to give the title object compound (0.10 g, 10%) as a pale-yellow solid.

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