反应详情

HATU (554 mg) was added to a solution of 5-bromo-N1-methylbenzene-1,2-diamine (279 mg), N,N-diisopropylethylamine (0.727 ml) and (1RS,2SR)-2-(methoxycarbonyl)cyclopropanecarboxylic acid (200 mg) in DMF (5 ml) at room temperature. The mixture was stirred at room temperature for 1 h. The mixture was quenched with water and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was dissolved in AcOH (5 ml), and the mixture was stirred at 80° C. for 1 h. After concentration of the mixture, the residue was neutralized with saturated NaHCO3 solution and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/EtOAc) to give the title compound (80 mg) as an off-white solid.

1. customThe mixture was quenched with water
2. extractionextracted with EtOAc
3. customThe organic layer was separated
4. washwashed with water and brine
5. dry with materialdried over MgSO4
6. concentrationconcentrated in vacuo
7. dissolutionThe residue was dissolved in AcOH (5 ml)
8. stirringthe mixture was stirred at 80° C. for 1 h
9. extractionextracted with EtOAc
10. customThe organic layer was separated
11. washwashed with water and brine
12. dry with materialdried over MgSO4
13. concentrationconcentrated in vacuo
14. customThe residue was purified by silica gel column chromatography (MeOH/EtOAc)