反应详情

To a solution of 4-(4-t-butoxycarbonylpiperazin-1-yl)benzoic acid (1.0 g, 3.3 mmol) and 1-(t-butoxycarbonylamino)-2-aminobenzene (Method 17, 0.68 g, 3.3 mmol) in DMF (10 ml) was added 4-(4,6-dimethoxy-1,3,5-triazinyl-2-yl)-4-methylmorpholinium chloride (1.1 g, 4.0 mmol) (Method 18). The mixture was stirred at ambient temperature for 20 hours. The mixture was concentrated in vacuo and the residue partitioned between water and ethyl acetate. The organic phase was separated and the aqueous reextracted with ethyl acetate. The combined organic extracts were dried over magnesium sulfate and evaporated. The residue was purified by flash chromatography (eluting with 4:1-1:1 isohexane/ethyl acetate). The product was dissolved in 1,4-dioxane (2.5 ml) and treated with a 4M solution of hydrogen chloride in 1,4-dioxane (2.5 ml). The mixture was stirred at ambient temperature for 4 hours. The resulting solid was collected by filtration, trated with a 2M aqueous solution of sodium hydroxide and extracted with ethyl acetate. The organic extract was dried over magnesium sulfate to afford the title compound as a colourless solid (176 mg, 92%); NMR Spectrum: (DMSO-d6) 2.89 (t, 4H), 3.25 (t, 4H), 4.90 (s, 2H), 6.66 (t, 1H), 6.84 (d, 1H), 7.01 (m, 3H), 7.21 (d, 1H), 7.92 (d, 2H), 9.48 (s, 1H); Mass Spectrum: M+H+ 297.

1. concentrationThe mixture was concentrated in vacuo
2. customthe residue partitioned between water and ethyl acetate
3. customThe organic phase was separated
4. dry with materialThe combined organic extracts were dried over magnesium sulfate
5. customevaporated
6. customThe residue was purified by flash chromatography (eluting with 4:1-1:1 isohexane/ethyl acetate)
7. dissolutionThe product was dissolved in 1,4-dioxane (2.5 ml)
8. additiontreated with a 4M solution of hydrogen chloride in 1,4-dioxane (2.5 ml)
9. stirringThe mixture was stirred at ambient temperature for 4 hours
10. filtrationThe resulting solid was collected by filtration
11. extractionextracted with ethyl acetate
12. extractionThe organic extract
13. dry with materialwas dried over magnesium sulfate