反应详情

To an ice cooled solution of N-(1-(3,4-dichlorophenyl)-1H-pyrazol-3-yl)-2-morpholinoacetamide (0.1 g, 0.28 mmol) in dry tetrahydrofurane (4 ml), in a dry nitrogen atmosphere, was dropwise added a 2M solution of borane dimethylsulfide in THF (0.7 ml, 1.4 mmol). The solution was slowly warmed to reflux, refluxed 4 hrs and additionally stirred at room temperature for 16 hrs. The mixture was ice cooled while water (2 ml) and 6M HCl (0.5 ml) cautiously added and, then, refluxed for 2 hrs. Solvents were coevaporated with methanol to dryness in vacuo. The crude residue was partitioned between 10% NaOH aqueous solution and ethyl acetate. The combined organic phases were washed with water, dried over sodium sulphate, filtered and evaporated to dryness yielding 94 mg of crude compound which was purified by column chromatography on silica gel (eluent:petroleum ether/ethyl acetate 50:50 to ethylacetate 100%). 1-(3,4-Dichlorophenyl)-N-(2-morpholinoethyl)-1H-pyrazol-3-amine (53 mg) was obtained as an oil.

1. temperatureThe solution was slowly warmed
2. temperatureto reflux
3. temperaturerefluxed 4 hrs
4. additioncautiously added
5. temperaturerefluxed for 2 hrs
6. customThe crude residue was partitioned between 10% NaOH aqueous solution and ethyl acetate
7. washThe combined organic phases were washed with water
8. dry with materialdried over sodium sulphate
9. filtrationfiltered
10. customevaporated to dryness
11. customyielding 94 mg of crude compound which
12. customwas purified by column chromatography on silica gel (eluent:petroleum ether/ethyl acetate 50:50 to ethylacetate 100%)