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A kind of synthetic method of 2-aminopyridine compounds

A synthesis method, aminopyridine technology, applied in the direction of organic chemistry, etc., can solve the problems of atomic diseconomy, complicated reaction steps, specific substitution position, etc., achieve the effect of light side reaction, simplified synthesis process, and improved yield

Inactive Publication Date: 2011-12-14
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] This method reduces the cost of the catalyst, reduces pollution, mild reaction conditions, and increases the yield. However, there are still problems such as difficult access to raw materials, complicated reaction steps, and few substituents, specific substitution positions, and uneconomical atoms.

Method used

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  • A kind of synthetic method of 2-aminopyridine compounds
  • A kind of synthetic method of 2-aminopyridine compounds
  • A kind of synthetic method of 2-aminopyridine compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] In a 50 ml round bottom flask, add 2 mmol 2-cyano-5-(4-methoxyphenyl)-2,4-pentadienenitrile, 2.1 mmol hydroxylamine hydrochloride, 10 ml dimethyl formaldehyde Amide; Stir at room temperature, add 4.4 mmol triethylamine at the same time, then stir the reaction system at 80°C for 3.5h, the reaction ends; after column chromatography, the white solid product 2-amino-3-cyano- 0.280 g of 6-(4-methoxyphenyl)pyridine, yield 62.2%. The reaction formula is as follows:

[0037]

[0038] Data characterization of the product:

[0039] Mp: 191~192℃;

[0040] 1 H NMR (400MHz, CDCl 3 , 25°C) δ=3.87(3H), 5.19(2H), 6.98(2H), .10(1H), 7.70, (1H), 7.94(2H);

[0041] 13 C NMR (125MHz, CDCl 3 , 25°C) δ=55.4, 88.4, 109.5, 114.2, 117.2, 128.8, 130.3, 141.7, 159.0, 160.0, 161.5.

[0042] It shows that the product is 2-amino-3-cyano-6-(4-methoxyphenyl)pyridine.

Embodiment 2

[0044] In a 50 milliliter round bottom flask, add 2 millimoles of 2-cyano-5-(4-chlorophenyl)-2,4-pentadienenitrile, 2.1 millimoles of hydroxylamine hydrochloride, and 10 milliliters of dimethylformamide; Stir at room temperature, add 4.4 mmol triethylamine at the same time, then stir the reaction system at 80°C for 3.5h, and the reaction ends; after column chromatography, the white solid product 2-amino-3-cyano-6- (4-Chlorophenyl)pyridine 0.290 g, yield 63.1%. The reaction formula is as follows:

[0045]

Embodiment 3

[0047] In a 50 ml round bottom flask, add 2 mmol 2-cyano-3-(3-methoxyphenyl)-2,4-pentadienenitrile, 2.1 mmol hydroxylamine hydrochloride, 10 ml dimethylformaldehyde Amide; Stir at room temperature, add 4.4 mmol triethylamine at the same time, then stir the reaction system at 80°C for 3.5h, and the reaction ends; the white solid product 2-amino-3-cyano-4-(3- 0.301 g of methoxyphenyl) pyridine, yield 66.8%. The reaction formula is as follows:

[0048]

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PUM

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Abstract

The invention provides a synthesis method of 2-amino pyridine compounds, belonging to the technical field of organic synthesis. The existing synthesis method has the disadvantages of difficult acquisition of raw materials, high catalyst cost, complicated reaction steps, harsh reaction conditions, serious environmental pollution, low yield, few substituent groups, specific substituent positions and atomic diseconomy. The synthesis method provided by the invention is characterized by comprising the following steps of: adding a 2,4-pentadiene nitrile compound and an amine compound in a molar ratio of 1.0:(1.0-2.5) to a solvent to form a reaction mixture; adding a base the amount of which is 0-250mol% of a substrate while stirring the reaction mixture; and then stirring at the temperature from room temperature to 150 DEG C for 3-24 hours to obtain a product namely the 2-amino pyridine compound. The synthesis method provided by the invention lowers the catalyst cost, relieves the pollution, simplifies the synthesis processes, has the advantages of mild reaction conditions, easy acquisition of raw materials, light side reaction, many substituent groups and wide application range, and has the yield of 58-81% depending on different reactions.

Description

technical field [0001] The invention relates to a method for synthesizing 2-aminopyridine compounds, using 2,4-pentadienenitrile compounds as five-carbon synthons, and synthesizing 2-aminopyridine in one step with ammonia compounds through [5C+1N] ring formation strategy Compounds, belonging to the technical field of organic synthesis. Background technique [0002] 2-aminopyridine compounds are important organic and pharmaceutical intermediates, which can be used to synthesize a variety of fine chemical and pharmaceutical products. For example, 2-amino 6-picoline can be used to make dyes and photographic developers; 2-amino-4-quinolyl-1,4-dihydropyridine compounds are a drug for treating cardiovascular diseases; 2- Amino-5-bromopyridine is used to synthesize phosphatidylinositol PI3 kinase inhibitors, aminopyridine derivatives selective dopamine D3 receptor agonists, and imidazo[1,2-a]pyridine compounds VEGFR-2 inhibitors, etc. Drugs can also be used to treat autoimmune di...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/85C07D213/803C07D213/80
Inventor 懂德文信晓庆梁永久张睿向德轩刘绪王自坤杨继明
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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