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Synthesis method of triazol pyridine ring compound

A technology for cyclic compounds and azolopyridines, applied in the field of synthesis of important potential drug molecules triazolopyridine ring compounds, can solve the problems of low yield, difficult storage of raw materials, high cost of highly toxic raw materials, and achieves easy operation and post-processing. safe effect

Inactive Publication Date: 2011-04-06
上海药明康德新药开发有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] The purpose of the present invention is to provide a synthesis method of an important drug molecule triazolopyridine ring compound, which mainly solves the problems of low yield or difficult storage of raw materials, use of highly toxic raw materials and high cost in existing synthesis methods.

Method used

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  • Synthesis method of triazol pyridine ring compound
  • Synthesis method of triazol pyridine ring compound
  • Synthesis method of triazol pyridine ring compound

Examples

Experimental program
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Effect test

Embodiment 1

[0022]

[0023] method one:

[0024] The synthetic technique of 6-(trifluoromethyl)-3-m-tolyl-[1,2,4]triazol[4,3-a]pyridine:

[0025] Add 5 milliliters of absolute ethanol, 0.144 grams of m-tolualdehyde (2, 1.2 mmol), 0.177 grams of 2-hydrazino-5-trifluoromethylpyridine (1, 1.0 mmol) in a 25 milliliter single-necked bottle ) was heated to reflux for 2 hours, monitored by TLC, and after the aromatic aldehyde disappeared substantially, it was cooled to room temperature. The white solid pyridylhydrazone Schiff base formed in the reaction was filtered off. Dissolve it in 8 ml of anhydrous toluene, add 1.2 mmol of lead tetraacetate, and heat and stir at 80°C for 18 hours. After cooling to room temperature, 5 ml of water was added, and the precipitated solid was filtered and dissolved in ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, brine, and dried over anhydrous sodium sulfate. Sodium sulfate was removed by filtration, the solvent was spun o...

Embodiment 2

[0032]

[0033] Replace m-methylbenzaldehyde in Example 1 with p-tolualdehyde to obtain 6-(trifluoromethyl)-3-p-tolyl-[1,2,4]triazol[4,3-a] Pyridine, the organic solvent is tetrahydrofuran, the reflux reaction time of the first step is 1 hour, and the reflux reaction time of the second step is 16 hours.

[0034] Yield: 78%. Its melting point: 108°C. H NMR spectrum 1 HNMR (CDCl 3 , 300MHz):: δ8.58(d, J=1.2Hz, 1H), 7.95(d, J=9.6Hz, 1H), 7.72(dd, J=1.8Hz, 6.6Hz, 2H), 7.46-7.38( m, 3H); mass spectrum (ESI source): C 14 h 10 f 3 N 3 m / z 278 (M + +1).

Embodiment 3

[0036]

[0037] Replace m-methylbenzaldehyde in Example 1 with o-methylbenzaldehyde to obtain 6-(trifluoromethyl)-3-o-tolyl-[1,2,4]triazol[4,3-a] Pyridine, the organic solvent is ethanol, the reflux reaction time of the first step is 1.5 hours, and the reflux reaction time of the second step is 20 hours.

[0038] Yield: 77%. Its melting point: 83°C. H NMR spectrum 1 HNMR (CDCl 3 , 300MHz):: δ8.16 (d, J = 1.2Hz, 1H), 7.98 (d, J = 9.6Hz, 1H), 7.56-7.40 (m, 5H); mass spectrum (ESI source): C 14 h 10 f 3 N 3 m / z 278 (M + +1).

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Abstract

The invention relates to a synthesis method of a triazol pyridine ring compound, which mainly solves the technical problems of low yield, high synthesizing cost, poor applicability and the like existing in the traditional synthesis method. The synthesis method comprises the following steps of: (1) making substituted 2-hydrazine-based pyridine react with substituted benzaldehyde, and (2) filtering sediments generated by reaction, dissolving the sediments in a solvent and adding lead tetraacetate, and refluxing to obtain a target product. The target product can be also obtained with a one-pot method by directly carry out the step (2) without separating the sediments. The synthesis method has the advantages of easy obtainment of simple raw materials, simple synthesizing steps, mild reaction condition and higher yield.

Description

Technical field: [0001] The invention relates to a synthesis method of a class of important potential drug molecule triazolopyridine ring compounds. Background technique: [0002] Triazole compounds are an important class of drug molecules, which can be used in pesticides as fungicides and plant growth regulators. For example, commercialized paclobutrazol and imabudazole have a strong growth-regulating effect on crops. In medicine, it has antibacterial, anti-inflammatory, anti-spasmodic, anti-platelet aggregation and other functions. As an important class of drug molecules, triazolopyridine ring compounds have been reported decades ago. [0003] These reports mainly include two types of synthetic methods: [0004] 1) The substituted 2-hydrazinopyridine reacts with the substituted aroyl chloride to generate a hydrazide, and then refluxes in phosphorus oxychloride to generate a triazolopyridine ring compound. [J.D. Bower and F.P. Doyle, Journal of the Chemical Society, 195...

Claims

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Application Information

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IPC IPC(8): C07D471/04
Inventor 廖江鹏林诗锐陈贵红肖贻崧贺海鹰陈曙辉
Owner 上海药明康德新药开发有限公司
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