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Preparation method of spiroindoline compound

A technology for indoline spiro and ring compounds, which is applied in the field of rapid preparation of indoline spiro compounds, achieving the effects of short synthesis route, high atom utilization rate and simple operation process

Inactive Publication Date: 2017-10-03
CHONGQING UNIV OF ARTS & SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The structure of the novel indoline spiro compound involved in the present invention has not yet been reported, and people's attention and research are urgently needed

Method used

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  • Preparation method of spiroindoline compound
  • Preparation method of spiroindoline compound
  • Preparation method of spiroindoline compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] where R 1 is aryl, R 2 is aryl, R 3 is an alkyl group, namely (±)-1-benzyl-3,6-diphenyl-1 H -imidazo[1',2':1,2]pyrrolo[3,2- b ]indole-2,5(3 H , 7 H )-diketone synthesis, the specific steps are as follows:

[0045] In a microwave reaction tube of 10 ml size, the 3-amino-1 H - Indole-1-carboxylate tert-butyl ester (1.0 mmol) and benzaldehyde (1.0 mmol) were dissolved in 2.0 mL of methanol solution, followed by benzoylformic acid (1.0 mmol) and benzylisocyanate (1.0 mmol) was added to the solution one by one, the reaction solution was stirred overnight at room temperature, and then the isocyanate was detected by thin-layer chromatography. If there was no remaining isocyanine raw material, the solution was dried with nitrogen, and then dissolved in 10% TFA / DCE (5 mL). In the microwave 100 o After reacting with C for 10 minutes, the reaction mixture was diluted with ethyl acetate (15 ml), washed with saturated sodium carbonate solution and sodium chloride solution ...

Embodiment 2

[0048] where R 1 is aryl, R 2 is aryl, R 3 is an alkyl group, namely (±)-1-benzyl-3-(3,4-dichlorophenyl)-6-phenyl-1 H -imidazo[1',2':1,2]pyrrolo[3,2- b ] indole-2,5 (3 H , 7 H )-diketone synthesis, the specific steps are as follows:

[0049] In a microwave reaction tube of 10 ml size, the 3-amino-1 H -Indole-1-carboxylate tert-butyl ester (1.0 mmol) and 3,4-dichlorobenzaldehyde (1.0 mmol) were dissolved in 2.0 mL of methanol solution, and then benzoylformic acid (1.0 mmol ) and benzyl isocyanide (1.0 mmol) were sequentially added to the solution, the reaction solution was stirred overnight at room temperature, and then the isocyanate was detected by thin-layer chromatography. If there was no remaining isocyanine raw material, the solution was dried with nitrogen, and Redissolve in 10% TFA / DCE (5 mL). In the microwave 100 o After reacting with C for 10 minutes, the reaction mixture was diluted with ethyl acetate (15 ml), washed with saturated sodium carbonate solution ...

Embodiment 3

[0052] where R 1 is aryl, R 2 is aryl, R 3 is an alkyl group, namely (±)-1-benzyl-3-(4-methoxyphenyl)-6-phenyl-1 H -imidazo[1',2':1,2]pyrrolo[3,2- b ]indole-2,5(3 H , 7 H )-diketone synthesis, the specific steps are as follows:

[0053] In a microwave reaction tube of 10 ml size, the 3-amino-1 H -Indole-1-carboxylate tert-butyl ester (1.0 mmol) and 4-methoxybenzaldehyde (1.0 mmol) were dissolved in 2.0 mL of methanol solution, followed by benzoylformic acid (1.0 mmol) and benzyl isocyanide (1.0 mmol) were sequentially added to the solution, the reaction solution was stirred overnight at room temperature, and then the isocyanate was detected by thin-layer chromatography. If there was no remaining isocyanine raw material, the solution was dried with nitrogen, and then Dissolve in 10% TFA / DCE (5 mL). In the microwave 100 o After reacting with C for 10 minutes, the reaction mixture was diluted with ethyl acetate (15 ml), washed with saturated sodium carbonate solution and...

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Abstract

The invention relates to a preparation method of a spiroindoline compound. The preparation method comprises that based on the Ugi reaction, carboxylic acid, aldehyde, 3-amino-1H-indole and an isocyanide as raw materials undergo a reaction under microwave irradiation to produce the novel spiroindoline compound. The preparation method is easy and fast, is easy to operate and is suitable for promotion and use.

Description

technical field [0001] The application relates to the field of drug synthesis, in particular to a rapid preparation method of an indoline spiro compound. Background technique [0002] The structure of the indoline spiro compound can be composed of indolinopiperidine, which has many pharmaceutical activities, such as growth hormone secretion agent, AKT kinase inhibitor, NK1 receptor antagonist, cathepsin inhibitor agent etc. It can have obvious therapeutic effects in the treatment of cardiovascular diseases and tumor diseases. [0003] The traditional synthesis method of indoline spiro compound is: with 4-piperidine carboxylic acid and phenylhydrazine, 2-fluorophenylacetonitrile, -2 hydroxyindole, halogenated aniline, piperidine carboxylic acid, tetrahydropyridinemethanol and three Fluazinamide is used as raw material for synthesis. However, the above synthesis steps are long and the post-processing process is complicated, which is not conducive to rapid synthesis. Howeve...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/20A61P35/00
CPCC07D487/20
Inventor 陈中祝徐志刚
Owner CHONGQING UNIV OF ARTS & SCI
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