反应 #45559

反应方程式

2-tert-Butyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-(3-nitrophenyl)-1,3-benzoxazole-4-carbonitrile

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compound

收率 17.1%

6-(3-Aminophenyl)-2-tert-butyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-1,3-benzoxazole-4-carbonitrile

收率 17.1%

溶剂

hydrogen chloride

反应条件

后处理

1. 1
   浓缩the solvent was concentrated under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in methanol (8 ml)
3. 3
   其他The catalyst was separated by filtration
4. 4
   浓缩the filtrate was concentrated under reduced pressure, aqueous 10% sodium carbonate solution and ethyl acetate
5. 5
   workup.ADDITIONwere added to the residue
6. 6
   其他The organic layer was collected by liquid-liquid separation
7. 7
   浓缩concentrated
8. 8
   其他purified by preparative TLC (developing solvent, chloroform:methanol=10:1)

实验过程

2-tert-Butyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-(3-nitrophenyl)-1,3-benzoxazole-4-carbonitrile (I-22) (30.7 mg, 68.6 μmol) was dissolved in 4 N hydrogen chloride (ethyl acetate solution, 2 ml) and the solvent was concentrated under reduced pressure. The residue was dissolved in methanol (8 ml), followed by catalytic hydrogenation at room temperature under normal pressure for 3 hours in the presence of 5% palladium-carbon (50% wet, 30 mg). The catalyst was separated by filtration, the filtrate was concentrated under reduced pressure, aqueous 10% sodium carbonate solution and ethyl acetate were added to the residue followed by stirring. The organic layer was collected by liquid-liquid separation, concentrated and purified by preparative TLC (developing solvent, chloroform:methanol=10:1) to obtain the entitled compound (4.9 mg) as a brown solid.

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