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Synthetic method of halogenated triazolopyridine

The technology of a halogenated triazolopyridine and a synthesis method is applied in the synthesis field of halogenated triazolopyridine, can solve problems such as low yield, and achieve the effects of simplifying purification steps, simplifying post-processing steps, and promoting heat dissipation

Pending Publication Date: 2022-07-22
上海泰坦科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In summary, the current synthetic method of triazolopyridine compounds has the problem of low yield

Method used

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  • Synthetic method of halogenated triazolopyridine
  • Synthetic method of halogenated triazolopyridine
  • Synthetic method of halogenated triazolopyridine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] A halogenated triazolopyridine, its concrete structural formula is:

[0063]

[0064] The synthetic method of above-mentioned a kind of halogenated triazolopyridine, the reaction equation of its synthetic process is as follows:

[0065]

[0066] The raw materials used in the above-mentioned synthesis reaction process and the corresponding raw material charging amount and charging ratio (the charging ratio is the amount of substance) are as follows:

[0067]

[0068] The synthetic method of above-mentioned a kind of halogenated triazolopyridine, the reaction steps of its synthetic process are as follows:

[0069] Synthesis of S1 compound of formula I-a:

[0070] 2-Amino-5-bromopyridine (15.0 g, 86.7 mmol) was added to isopropanol (320 ml) to obtain mixed solution A; DMF-DMA (12.4 g, 104.0 mmol) was added to mixed solution A to obtain mixed solution B; the mixed solution B is controlled to react at 85° C. under the conditions of reflux and mechanical stirring f...

Embodiment 2

[0078] A halogenated triazolopyridine, its concrete structural formula is:

[0079]

[0080] The synthetic method of above-mentioned a kind of halogenated triazolopyridine, the reaction equation of its synthetic process is as follows:

[0081]

[0082] The raw materials used in the above-mentioned synthesis reaction process and the corresponding raw material charging amount and charging ratio (the charging ratio is the amount of substance) are as follows:

[0083]

[0084]

[0085] The synthetic method of above-mentioned a kind of halogenated triazolopyridine, the reaction steps of its synthetic process are as follows;

[0086] Synthesis of S1 compound of formula I-b:

[0087] 2-Amino-4-bromopyridine (15.0 g, 86.7 mmol) was added to isopropanol (320 ml) to obtain mixed solution A; DMF-DMA (12.4 g, 104.0 mmol) was added to mixed solution A to obtain mixed solution B; the mixed solution B is controlled to react at 85° C. under the conditions of reflux and mechanica...

Embodiment 3

[0095]A halogenated triazolopyridine, its concrete structural formula is:

[0096]

[0097] The synthetic method of above-mentioned a kind of halogenated triazolopyridine, the reaction equation of its synthetic process is as follows:

[0098]

[0099] The raw materials used in the above-mentioned synthesis reaction process and the corresponding raw material charging amount and charging ratio (the charging ratio is the amount of substance) are as follows:

[0100]

[0101] The synthetic method of above-mentioned a kind of halogenated triazolopyridine, the reaction steps of its synthetic process are as follows;

[0102] Synthesis of S1 compounds of formula I-c:

[0103] 2-Amino-3-bromopyridine (15.0 g, 86.7 mmol) was added to isopropanol (320 ml) to obtain mixed solution A; DMF-DMA (12.4 g, 104.0 mmol) was added to mixed solution A to obtain mixed solution B; the mixed solution B is controlled to react at 85° C. under the conditions of reflux and mechanical stirring f...

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Abstract

The invention relates to the technical field of organic synthesis, in particular to a synthetic method of halogenated triazolopyridine. The invention relates to a synthetic method of halogenated triazolopyridine, which comprises the following steps of: carrying out condensation reaction on a compound represented by the following formula I and trifluoroacetic anhydride serving as raw materials and toluene serving as a solvent at the temperature of 20-25 DEG C to obtain a reaction solution; controlling the temperature of the obtained reaction liquid to be-5-0 DEG C, adjusting the pH value of the reaction liquid to be 9-10 under a stirring condition, separating out a solid from the reaction liquid, filtering and collecting the separated solid, washing the solid with water until the pH value is 7, and drying the solid to obtain halogenated triazolopyridine; the synthesis method provided by the invention has the effects of promoting synthesis of the target product, simplifying purification steps of the target product and improving the yield of the target product.

Description

technical field [0001] The present application relates to the technical field of organic synthesis, and more particularly, to a method for synthesizing halogenated triazolopyridines. Background technique [0002] Imidazopyridines have special structures similar to indole, azaindole, etc. and good biological activities. Generally, imidazopyridines can be used to treat autoimmune diseases, inflammatory diseases, cardiovascular diseases or neurodegenerative diseases. , so it has a wide range of applications in the pharmaceutical and pesticide industries. Among them, triazolopyridine compounds also have a wide range of uses in biology, such as synthesis of ask inhibitors, as prolyl hydroxylase inhibitors and erythropoietin production inducers, as JAK kinase inhibitors and so on. Meanwhile, triazolopyridine compounds and pharmaceutical compositions containing them can also be used to treat diseases related to JAK kinase activity, such as inflammation, autoimmune disorders, cance...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 谢应波张庆张华罗桂云曹云藏睿
Owner 上海泰坦科技股份有限公司