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A kind of arylamine derivative containing alkyne group and its preparation method and application

A technology for arylamines and derivatives, which is applied in the field of arylamine derivatives and their preparation, can solve the problems of limited types of arylamine derivatives, achieve good application prospects, and enrich the effect of chemical activity

Active Publication Date: 2022-01-11
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the development of new drug molecules, there is still a problem that the types of arylamine derivatives are limited and need to be broadened

Method used

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  • A kind of arylamine derivative containing alkyne group and its preparation method and application
  • A kind of arylamine derivative containing alkyne group and its preparation method and application
  • A kind of arylamine derivative containing alkyne group and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] The present embodiment carries out the preparation of N-(2-((triisopropylsilyl)ethynyl)benzyl)trifluoromethanesulfonamide (3a), and its reaction formula is as follows:

[0088]

[0089] Under an atmospheric pressure air atmosphere, arylamine compound 1a (48.0mg, 0.20mmol), divalent palladium metal catalyst Pd(OAc) was added sequentially to a 15mL Schlenk reaction tube 2 (0.9mg, 0.004mmol), N-tert-butoxycarbonyl-leucine (N-Boc-Leu) (2.3mg, 0.01mmol), sodium acetate (2.5mg, 0.03mmol), silver acetate (10.0mg, 0.06 mmol), use a syringe to inject a solution of triisopropylsilylacetylene bromide 2a (20 μL, 0.30 mmol) in 1,2-dichloroethane (DCE, 1 mL) into the reactor, and react at a temperature of 100 ° C for 12 h , cooled to room temperature after the reaction, filtered through diatomaceous earth, and concentrated using a rotary evaporator to obtain a crude product. The crude product was separated by chromatography on a prepared silica gel plate, and the selected develop...

Embodiment 2

[0093] The present embodiment carries out the preparation of N-(2-chloro-6-((triisopropylsilyl)ethynyl)benzyl)trifluoromethanesulfonamide (3b), and its reaction formula is as follows:

[0094]

[0095] Under an atmosphere of atmospheric pressure air, arylamine compound 1b (54.6mg, 0.20mmol), divalent palladium metal catalyst Pd(OAc) were sequentially added to a 15mL Schlenk reaction tube 2 (2.25mg, 0.01mmol), N-tert-butoxycarbonyl-leucine (N-Boc-Leu) (6.90mg, 0.03mmol), sodium acetate (0.82mg, 0.10mmol), silver acetate (33.4mg, 0.20 mmol), use a syringe to inject a solution of triisopropylsilylacetylene bromide 2a (26 μL, 0.40 mmol) in 1,2-dichloroethane (DCE, 1 mL) into the reactor, and react at a temperature of 100 ° C for 12 h . After the reaction was completed, it was cooled to room temperature, filtered through diatomaceous earth, and concentrated using a rotary evaporator to obtain a crude product. The crude product was separated by chromatography on a prepared sili...

Embodiment 3

[0099] In this example, the preparation of N-(4-fluoro-2-((triisopropylsilyl)ethynyl)benzyl)trifluoromethanesulfonamide (3c) is carried out, and its reaction formula is as follows:

[0100]

[0101] Under an atmosphere of atmospheric pressure air, arylamine compound 1c (52.0mg, 0.20mmol), divalent palladium metal catalyst Pd(OAc) were sequentially added to a 15mL Schlenk reaction tube 2 (0.9 mg, 0.004 mmol), N-tert-butoxycarbonyl-leucine (2.30 mg, 0.01 mmol), sodium acetate (2.5 mg, 0.03 mmol), silver acetate (10.0 mg, 0.06 mmol), inject three A solution of isopropylsilylacetylene bromide 2a (20 μL, 0.30 mmol) in 1,2-dichloroethane (DCE, 1 mL) was put into the reactor, and reacted at 100° C. for 12 h. After the reaction was completed, it was cooled to room temperature, filtered through diatomaceous earth, and concentrated using a rotary evaporator to obtain a crude product. The crude product was chromatographically separated on a prepared silica gel plate, and the selected...

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Abstract

The invention belongs to the technical field of organic synthesis, and in particular relates to an alkynyl-containing arylamine derivative and a preparation method and application thereof. The present invention provides an alkynyl-containing arylamine derivative, the structural formula of the alkynyl-containing arylamine derivative is shown in formula (I); wherein, Ar is an aryl group, including an aromatic heterocycle Base, phenyl or aromatic fused ring group; R 1 selected from hydrogen, halogen, hydrocarbyl or substituted hydrocarbyl; R 2 It is a multi-substituted silicon group. The arylamine derivatives of the present invention introduce a multifunctional alkynyl group, and the alkynyl group is located in the ortho position of the amine group on the aryl group. In view of the abundant chemical activity of the carbon-carbon triple bond of the alkynyl group, and the arylamine Widely used in medicines, the alkynyl-containing arylamine derivatives of the present invention have good application prospects in medicine development.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to an alkynyl-containing arylamine derivative and a preparation method and application thereof. Background technique [0002] As a kind of functional group that is ubiquitous in organic synthesis and human production and life, amines have a profound impact on human life, from amino acids that make up proteins to natural products that exist widely in nature, as well as nitrogen-containing drugs and materials that cure diseases. Heterocycles, polysubstituted amines, etc., amine compounds are extremely important. Since Harper's ammonia synthesis process, human beings have been continuously interested in the rapid and universal construction of amine compounds. Efforts are underway to synthesize, and methods of, biologically active amine derivatives. [0003] Arylamine derivatives, as important skeletons of biologically active molecules, widely exist in drug molec...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/08
Inventor 聂坚宏李先纬霍延平
Owner GUANGDONG UNIV OF TECH
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