反应详情

To a solution of 2-chloro-3-(1-cyanocyclopropyl)benzoic acid (237 mg, 1.07 mmol) in tetrahydrofuran (4 mL) were added oxalyl chloride (170 mg, 1.34 mmol) and N,N-dimethylformamide (10 μL), and the mixture was stirred for 1 hr. The reaction mixture was concentrated under reduced pressure, and the obtained residue was dissolved in N,N-dimethylacetamide (4 mL). N-[6-(3-Aminophenoxy)-1,3-benzothiazol-2-yl]acetamide (160 mg, 0.534 mmol) was added and the mixture was stirred at room temperature for 2 hr. To the reaction mixture were added water (100 mL) and ethyl acetate (100 mL). The organic layer was separated, washed with saturated brine (10 mL), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→0/100), and triturated with ethyl acetate/diisopropyl ether to give the title compound (215 mg, 80%) as a yellow solid.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. dissolutionthe obtained residue was dissolved in N,N-dimethylacetamide (4 mL)
3. stirringthe mixture was stirred at room temperature for 2 hr
4. customThe organic layer was separated
5. washwashed with saturated brine (10 mL)
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationThe insoluble material was filtered off
8. concentrationthe filtrate was concentrated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→0/100)
10. customtriturated with ethyl acetate/diisopropyl ether