Unlock instant, AI-driven research and patent intelligence for your innovation.

3,4,5-trisubstituted-1h-pyrazole compound and its synthesis method

A technology for compounds and pyrazoles, applied in the field of 3,4,5-trisubstituted-1H-pyrazoles and their synthesis, can solve the problems of poor product regioselectivity, difficult synthesis of raw materials, etc., and achieve post-processing The effect of simplicity, mild reaction conditions and good development prospects

Active Publication Date: 2017-01-04
SHANGHAI MACKLIN BIOCHEM TECH
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] In summary, there are several methods for the preparation of polysubstituted pyrazoles, but some of the reaction methods have their limitations and shortcomings, such as poor product regioselectivity, use of noble metals as catalysts, etc., and the above-mentioned several This kind of method all needs to introduce corresponding substituting group in reactant molecule in advance and just can realize when synthesizing 4-substituted pyrazoles, has caused the difficulty of synthetic raw material

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 3,4,5-trisubstituted-1h-pyrazole compound and its synthesis method
  • 3,4,5-trisubstituted-1h-pyrazole compound and its synthesis method
  • 3,4,5-trisubstituted-1h-pyrazole compound and its synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1: 3-(4-methoxyphenyl)-5-phenyl-4-acetoxy-1 H - Preparation of pyrazole

[0042] 3-(4-methoxyphenyl)-5-phenyl-4-acetoxy-1H-pyrazole adopts the following steps: 1. add 38.84 grams (2-((anti)- 1-(4-methoxyphenyl)-3-phenylallylidene)hydrazino) diethyl phosphite, 1.35 g anhydrous copper chloride, 7.21 g acetic acid, 16.58 g anhydrous potassium carbonate, 500 ml Dimethyl sulfoxide, in an oxygen atmosphere at 50-60 oStir at C. Use thin layer chromatography to track the reaction until the raw materials disappear; ② After the reaction, add saturated sodium chloride solution to the system, extract the product with ethyl acetate, and remove the solvent with a rotary evaporator after drying to obtain a crude product; ③ The crude product was purified by column chromatography (petroleum ether: ethyl acetate = 10: 1) to obtain 21.58 g of 3-(4-methoxyphenyl)-5-phenyl-4-acetoxy-1H-pyrazole , and the yield was 75%. Melting point: 174-176 o c.

[0043] –1 ): 3228, 2861, 1...

Embodiment 2

[0048] Example 2: 3-(3-Chlorophenyl)-5-phenyl-4-acetoxy-1 H - Preparation of pyrazole

[0049] 3-(3-Chlorophenyl)-5-phenyl-4-acetoxy-1 H -Pyrazole adopts the following steps: 1. add 39.28 grams (2-((trans)-1-(3-chlorophenyl)-3-phenylallylidene) hydrazine) phosphorous acid di Ethyl ester, 1.35 grams of anhydrous copper chloride, 7.21 grams of acetic acid, 16.58 grams of anhydrous potassium carbonate, 500 milliliters of dimethyl sulfoxide, in an oxygen atmosphere at 50-60 o Stir at C. Use thin layer chromatography to track the reaction until the raw materials disappear; ② After the reaction, add saturated sodium chloride solution to the system, extract the product with ethyl acetate, and remove the solvent with a rotary evaporator after drying to obtain a crude product; ③ The crude product was purified by column chromatography (petroleum ether: ethyl acetate = 10: 1) to obtain 20.95 g of 3-(3-chlorophenyl)-5-phenyl-4-acetoxy-1 H - pyrazole, the yield is 67%. Melting point: ...

Embodiment 3

[0055] Example 3: 3-(4-bromophenyl)-5-phenyl-4-acetoxy-1 H - Preparation of pyrazole

[0056] 3-(4-Bromophenyl)-5-phenyl-4-acetoxy-1 H -pyrazole adopts the following steps: 1. add 43.73 grams (2-((anti)-1-(4-bromophenyl)-3-phenylallylidene)hydrazine)phosphite di Ethyl ester, 1.35 grams of anhydrous copper chloride, 7.21 grams of acetic acid, 16.58 grams of anhydrous potassium carbonate, 500 milliliters of dimethyl sulfoxide, in an oxygen atmosphere at 50-60 o Stir at C. Use thin layer chromatography to track the reaction until the raw materials disappear; ② After the reaction, add saturated sodium chloride solution to the system, extract the product with ethyl acetate, and remove the solvent with a rotary evaporator after drying to obtain a crude product; ③ The crude product was purified by column chromatography (petroleum ether: ethyl acetate = 10: 1) to obtain 23.58 g of 3-(4-bromophenyl)-5-phenyl-4-acetoxy-1 H - pyrazole, the yield is 66%. Melting point: 239-241 o c. ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to a 3,4,5-trisubstituted-1H-pyrazole compound and a preparation method thereof. The structural formula of the compound is: . Wherein, R1=H, OMe, Cl, Br; R2=H, Br; R3=o-MeC6H4, p-OMeC6H4, cyclohexyl, t-butyl. The raw material of the method of the invention is easy to obtain, the cost is low, and the substrate has a wide application range. Conventional solvents are used in the reaction, the operation is simple, the conditions are mild, the reaction is environmentally friendly, and the reaction yield reaches 70%, which is very suitable for industrial production.

Description

technical field [0001] The present invention relates to a kind of pyrazole compound and its synthetic method, especially a kind of 3,4,5-trisubstituted-1 H - Pyrazole compounds and their synthesis methods. Background technique [0002] Heterocyclic compounds have always been one of the research hotspots in the field of organic chemistry. They occupy a very important position in the research and development of medicines and pesticides. Their wide range of biological activities and variable structure types have attracted widespread attention. Most of them are artificially synthesized heterocyclic compounds, which play a pivotal role in the field of biomedicine. [0003] Nitrogen-containing heterocycle is a very common pharmacophore in the field of drug research, and it is one of the important targets of small molecule drug development today. Many of the top-selling branded drugs in the world have nitrogen-containing heterocyclic skeletons. Among the numerous nitrogen-contai...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/18
Inventor 许斌丁正伟陈欢欢刘秉新谭启涛
Owner SHANGHAI MACKLIN BIOCHEM TECH