Sodium Iodide → HCID 66778303, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-[chloro(cyclohexyl)methyl]-1-methyl-1H-indazole (465 mg) synthesized above, ethyl 3-{[(4-aminophenyl)carbonyl](methyl)amino}propanoate (531 mg) synthesized in Example 2(2), sodium iodide (531 mg) and N,N-dimethylacetamide (10 mL) was added sodium carbonate (375 mg), and the mixture was stirred under argon atmosphere at 100° C. overnight. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:2, volume ratio) to give a white solid. To a mixture of the obtained solid, tetrahydrofuran (5 mL) and ethanol (5 mL) was added 1N aqueous sodium hydroxide solution (2.00 mL), and the mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in water (10 mL), and 1N hydrochloric acid (2.00 mL) was added at 0° C. The resulting precipitate was collected by filtration to give the title object compound (356 mg, 45%) as a white solid.

Provenance & Evidence