1-Iodohexane → 6,8-Difluoro-2-[4-(N,N-dimethylamino)-3-fluorophenyl]-5-hexylamino-4H-1-benzopyran-4-one

Participants

Reaction Steps

500 mg (1.50 mmol) of Compound 38 obtained in Example 38 was dissolved in 5 ml of dimethylformamide under argon atmosphere, 120 mg of sodium hydride (60% oil disperison) and 0.441 ml of 1-iodohexane were added under ice-cooling and the mixture was stirred at room temperature for 3 hours. An aqueous saturated solution of ammonium chloride was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:1) and recrystallized from n-hexane/ethyl acetate to give Compound 58 which was converted into hydrochloride according to the same manner as that in Example 16 to give 494 mg (79%).

Provenance & Evidence