反应详情

To a mixture of 5-[4-[6-[4-(2-aminoethyl)phenoxy]-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride (0.3 g), triethylamine (0.17 g) and anhydrous N,N-dimethylformamide (10 ml) was added 2,4,6-triisopropylbenzenesulfonyl chloride (0.17 g) and the mixture was stirred at room temperature for 4.5 hours. The reaction mixture was concentrated and partitioned between ethyl acetate and water. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated. The residue was chromatographed on a silica gel column using ethyl acetate:n-hexane=2:1 as the eluant. To a solution of the product in ethyl acetate (15 ml) was added 4N hydrogen chloride in 1,4-dioxane (2 ml) and the mixture was stirred at room temperature for 20 minutes. The precipitate was isolated by filtration and washed with ethyl acetate to afford the title compound (0.28 g, mp 134-136° C.).

1. concentrationThe reaction mixture was concentrated
2. custompartitioned between ethyl acetate and water
3. washThe extract was washed with saturated aqueous sodium chloride solution
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated
6. customThe residue was chromatographed on a silica gel column
7. additionTo a solution of the product in ethyl acetate (15 ml) was added 4N hydrogen chloride in 1,4-dioxane (2 ml)
8. stirringthe mixture was stirred at room temperature for 20 minutes
9. customThe precipitate was isolated by filtration
10. washwashed with ethyl acetate