Cyclopropanecarbonyl chloride → 3-(1-cyano-1-methylethyl)-N-[3-({2-[(cyclopropylcarbonyl)amino]-1,3-benzothiazol-6-yl}oxy)phenyl]benzamide

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Reaction Steps

To a solution of N-{3-[(2-amino-1,3-benzothiazol-6-yl)oxy]phenyl}-3-(1-cyano-1-methylethyl)benzamide (5.13 g, 12.0 mmol) in pyridine (50 mL) were added cyclopropanecarbonyl chloride (2.5 mL, 27.6 mmol) and N,N-dimethylpyridine-4-amine (89.3 mg, 731 μmol), and the mixture was stirred at room temperature for 6 hr. The reaction mixture was diluted with methanol (50 mL), 2N aqueous sodium hydroxide solution (10 mL) was added, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated under reduced pressure, and the residue was suspended in ethyl acetate (300 mL), and washed successively with water (150 mL), dilute hydrochloric acid (100 mL), saturated aqueous sodium hydrogencarbonate solution (100 mL) and saturated brine (100 mL), successively. The organic layer was 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 chromatography (hexane/ethyl acetate=95/5→50/50) and recrystallized from ethyl acetate/diisopropyl ether to give the title compound (4.4 g, 88%) as colorless crystals.

Provenance & Evidence