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Ester-based pyrazole bithiazole amine compound as well as preparation method and application thereof

A technology of ester-based pyrazole-bithiazolamide and compounds, which is applied in the field of medicinal chemistry and can solve the problems of repetition and low reaction economy

Inactive Publication Date: 2020-09-01
WUHAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this method, structural diversification is realized in the early stage of synthesis. Each synthesis of a target product with different substituents must be synthesized from raw materials. The synthesis steps are often repeated, and the reaction economy is not high.

Method used

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  • Ester-based pyrazole bithiazole amine compound as well as preparation method and application thereof
  • Ester-based pyrazole bithiazole amine compound as well as preparation method and application thereof
  • Ester-based pyrazole bithiazole amine compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Synthesis of the compound of Example 1

[0017] The compound structural formula is:

[0018] ,

[0019] where in example compounds R 1 =CH 3 , R 2 =R 4 =R 5 =R 6 =H,R 3 =Et.

[0020] The compound can be prepared by the following preparation scheme, and the reaction scheme is as follows:

[0021] .

[0022] Specific synthesis steps:

[0023] (a) Preparation of compound 2

[0024]

[0025] Compound 1 (8.1 g, 51.9 mmol) was added to tetrahydrofuran THF (260 ml) under ice bath, followed by triethylamine (28.86 ml, 207.62 mmol), 4-dimethylaminopyridine DMAP (95.12 mg, 778.57 μmol), respectively ), after 10 min, di-tert-butyl dicarbonate (Boc) was added dropwise 2 O (71.62 ml, 311.43 mmol), continue stirring for 10 min, remove the ice bath, and heat under reflux for 5 h. The filtrate was obtained by suction filtration and the solvent was spun to obtain a solid. After drying, DMF was added to dissolve, water was added, suction filtration, and drying were p...

Embodiment 2

[0035] The application of embodiment 2 compound in the synthesis of aromatic ring-thiazole-pyrazole organic acid

[0036] The general structural formula of aromatic ring-thiazole-pyrazole organic acid compounds is:

[0037] .

[0038] R in the above formula 7 At least hydrogen, C 1 -C 4 Saturated or unsaturated alkyl, saturated or unsaturated alkoxy, halogen, aryl (benzene ring and substituted benzene ring); the reaction scheme is:

[0039] .

[0040] The specific synthesis steps are:

[0041] (a) Preparation of compound 6

[0042]

[0043] The aromatic acid (1 equiv) with different substituents was dissolved in DMF, reacted with CDI (1.3 euquiv) for 30 min, then compound 5 (1 equiv) was added, and the reaction was heated under reflux for 15 h. After the reaction was completed, it was cooled to room temperature, water was added, the solid was filtered, and dried to obtain compound 6 with a yield of 80%.

[0044] when R 7 When H, the compound structural formula ...

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Abstract

The invention discloses an ester-based pyrazole bithiazole amine compound as well as a preparation method and application thereof. The structural general formula of the ester-based pyrazole bithiazoleamine compound is shown in the specification. The compound is a double-five-membered nitrogen heterocyclic bifunctional compound, is convenient for realizing high-throughput synthesis and diversifiedderivation of thiazole amine and pyrazole, and can be widely applied to the research, development and production of thiazole bipyrazole drugs.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to ester pyrazole bithiazolamine and a preparation method and application thereof. Background technique [0002] Thiazole and pyrazole are common compound groups in medicinal chemistry, and the resulting derivatives have good biological activities, such as anti-cancer cell migration, anti-fungal, and anti-proliferation. Aromatic ring-thiazole-pyrazole organic acid is used as a pharmaceutical active intermediate, and it is necessary to synthesize intermediates with different substituents on the aromatic ring. The current route for synthesizing aromatic ring-thiazole-pyrazole organic acids is that aromatic (including heteroaromatic) acids with different substituents first undergo amide condensation with aminothiazolones, and then undergo Claisen condensation and pyrazole ring formation respectively. reaction and ester hydrolysis to obtain (Long Ye, John M. Knapp, Panjamap...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/04
CPCC07D417/04
Inventor 叶龙彭万才邵辉唐关平
Owner WUHAN UNIV OF SCI & TECH