反应详情

A mixture of 4-morpholin-4-ylmethyl-benzene-1,2-diamine (2.5 g, 12 mmol), 1-(4-methoxy-benzyl)-4-nitro-1H-pyrazole-3-carboxylic acid (2.91 g, 10 mmol), EDC (2.3 g, 12 mmol) and HOBt (1.62 g, 12 mmol) in dry DMF (40 ml) was stirred at ambient temperature for 24 h. The mixture was reduced in vacuo, the residue partitioned between EtOAc (100 ml) and water (50 ml) and the organic portion washed with saturated aqueous sodium hydrogen carbonate, dried (MgSO4) and reduced in vacuo. The residue was dissolved in AcOH (70 ml) and heated at reflux for 3 h. The solvent was removed in vacuo and the residue purified by flash column chromatography [SiO2, MeOH:DCM (5:95)] to give 2-[1-(4-methoxy-benzyl)-4-nitro-1H-pyrazol-3-yl]-5-morpholin-4-ylmethyl-1H-benzimidazole (2 g, 37%) as a yellow foam. (LC/MS: Rt 1.91, [M+H]+ 449).

1. customthe residue partitioned between EtOAc (100 ml) and water (50 ml)
2. washthe organic portion washed with saturated aqueous sodium hydrogen carbonate
3. dry with materialdried (MgSO4)
4. dissolutionThe residue was dissolved in AcOH (70 ml)
5. temperatureheated
6. temperatureat reflux for 3 h
7. customThe solvent was removed in vacuo
8. customthe residue purified by flash column chromatography [SiO2, MeOH:DCM (5:95)]