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4-(N,N-dimethyl) aminopyridine derivate and synthesis method thereof

A technology of dimethylaminopyridine and aminopyridine is applied in the field of 4-aminopyridine derivatives and synthesis thereof, and can solve the problems of high synthesis cost and remote practical application.

Inactive Publication Date: 2010-11-24
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0025] In summary, although many DMAP analogues have been synthesized, the synthesis process requires either multi-step reactions, or the harsh conditions of anhydrous and oxygen-free ultra-low temperature, and the participation of metal-organic reagents. Therefore, the synthesis cost is very high, even if the catalyst has good catalytic performance, it is still far away from practical application

Method used

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  • 4-(N,N-dimethyl) aminopyridine derivate and synthesis method thereof
  • 4-(N,N-dimethyl) aminopyridine derivate and synthesis method thereof
  • 4-(N,N-dimethyl) aminopyridine derivate and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Example 1: Add 0.126g (0.60mmol) of 3-bromo-4-(N,N-dimethyl)aminopyridine into a 5mL polytetrafluoroethylene autoclave, then add 0.030mmol triphenylphosphorous palladium catalyst, 3.0 1 mmol olefinic compound and 6.0 mmol triethylamine, put the autoclave into an oven and heat to 120° C., and react for 24 hours. After stopping the reaction, cool to room temperature, add 10mL of dichloromethane and 10mL of water, separate the organic layer, extract with dichloromethane (10mL x 3), dry the organic layer with anhydrous sodium sulfate, filter the organic phase, and remove it under reduced pressure. solvent, and the residue was purified by thin layer chromatography to obtain the product. For the alkenes used and the reaction results, please refer to Table 1

[0051] Table 1 Alkenes and their reaction results

[0052]

[0053] Characterization parameters of each product:

[0054] 1. The structural formula of product 1:

[0055] yellow liquid.

[0056] 1 H-NMR (CDCl ...

Embodiment 2

[0085] Example 2: Synthesis of (S)-3-(4-N,N-dimethylaminopyridine-3-)-N-(1-phenylethyl)-acrylamide

[0086] Add 0.100 g (0.50 mmol) of 3-bromo-4-(N,N-dimethyl)aminopyridine into a 5 mL polytetrafluoroethylene autoclave, then add 0.025 mmol Pd catalyst, 0.60 mmol (S)-N-( 1-phenylethyl)-acrylamide and 5.00 mmol of acid-binding agent triethylamine TEA, put the autoclave into an oven and heat to a certain temperature, and react for 24 hours. After stopping the reaction, cool to room temperature, add 10mL dichloromethane and 10mL water, separate the organic layer, then extract with dichloromethane (10mL x3), dry the organic layer with anhydrous sodium sulfate, filter the organic phase, and The solvent was removed, and the residue was purified by thin layer chromatography (dichloromethane:ethanol=9.8:0.2) to obtain the product (S)-3-(4-N,N-dimethylaminopyridine-3-)-N-(1 -phenylethyl)-acrylamide, productive rate 43%, its structural formula is:

[0087]

[0088] yellow solid.

...

Embodiment 3

[0091] Example 3: Synthesis of (S)-1-[3-(4-dimethylaminopyridine-3-)-acryloyl]-pyrrolidine-2-carboxylic acid ethyl ester 8:

[0092] Add 0.100 g (0.50 mmol) of 3-bromo-4-(N,N-dimethyl)aminopyridine into a 5 mL polytetrafluoroethylene autoclave, then add 0.025 mmol of Pd catalyst, 0.60 mmol of (S)-1-propylene Acylpyrrolidine-2-carboxylic acid ethyl ester and 5.00mmol acid-binding agent TEA, put the autoclave into an oven and heat to a certain temperature, and react for 24 hours. After stopping the reaction, cool to room temperature, add 10mL of dichloromethane and 10mL of water, separate the organic layer, then extract with dichloromethane (10mL x 3), dry the organic layer with anhydrous sodium sulfate, filter the organic phase, and depressurize The solvent was removed, and the residue was purified by thin layer chromatography (dichloromethane:ethanol=9.8:0.2) to obtain product 8, namely (S)-1-[3-(4-dimethylaminopyridine-3-)- Acryloyl]-pyrrolidine-2-carboxylic acid ethyl ester...

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Abstract

The invention relates to a 4-(N,N-dimethyl) aminopyridine derivate and a synthesis method thereof. The derivate has a structural formula shown in the specification of the invention, wherein R is -PH and -CN. Under the more common condition or microwave condition, the invention synthesizes 11 4-(N,N-dimethyl) aminopyridine derivates with higher yields. A chiral N,N dimethyl aminopyridine analogue is applied to asymmetric kinetic resolution of secondary alcohol 1-phenylethanol to obtain a medium value of ee percent.

Description

technical field [0001] The invention relates to a 4-(N,N-dimethyl)aminopyridine derivative and a synthesis method thereof. Background technique [0002] Organic small molecule chiral catalysis uses chiral organic small molecules to directly catalyze reactions without the participation of metals, and its mode of action is similar to that of enzymes. Therefore, small organic molecule catalysts are often referred to as artificial enzymes or enzyme analogs. They are an important class of asymmetric catalysts after transition metal catalysts, and a chiral catalyst that has developed rapidly in the past decade. [0003] In the past two decades, organometallic catalysts have been mainly used in the field of chiral synthesis, and chiral metal complex catalysis has almost become synonymous with asymmetric catalysis. Chiral metal complexes can form a variety of chiral catalysts by changing the type of transition metal or modification of chiral ligands, and there are many types of cat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/74C07D401/06C07D413/06B01J31/02C07C69/157C07C67/08
Inventor 林昆华钟燕华余喆吟曾庆彬龚和贵王洪宇
Owner SHANGHAI UNIV
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