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Synthesis method of 3-ethyl carboxylate-4-chloro imidazole [1,5-a] quinoxaline

A technology of ethyl carboxylate and a synthesis method, applied in the direction of organic chemistry and the like, can solve the problems of expensive reaction raw materials, lack of synthesis routes, and poor applicability, and achieves the effects of short steps, simple purification, and easy amplification.

Inactive Publication Date: 2012-04-18
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

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Problems solved by technology

It mainly solves technical problems such as the lack of existing synthetic routes and the existence of expensive reaction raw materials, difficult amplification, and limited applicability.

Method used

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  • Synthesis method of 3-ethyl carboxylate-4-chloro imidazole [1,5-a] quinoxaline
  • Synthesis method of 3-ethyl carboxylate-4-chloro imidazole [1,5-a] quinoxaline
  • Synthesis method of 3-ethyl carboxylate-4-chloro imidazole [1,5-a] quinoxaline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1 : 2,3-Dihydroxyquinoxaline The synthesis process:

[0022]

[0023] In a 1 liter reaction flask equipped with a reflux condenser, o-phenylenediamine (50 g, 0.46 mol) was dissolved in ethanol (500 ml), and diethyl oxalate (135.1 g, 0.92 mol) was added with stirring. The reaction was slowly heated to reflux (78°C). After 12 hours, the reaction was completed. The reaction was cooled in an ice-water bath, and the precipitated solid was filtered. The filter cake was washed with cold ethanol (100 ml x 2) and dried in vacuo The target product 2,3-dihydroxyquinoxaline (67 g, 87%) was obtained.

[0024] H NMR spectrum (DMSO- d 6 , 400 MHz), δ ppm: 11.91 (s, 2 H), 7.11-7.06 (m, 4 H).

Embodiment 2

[0025] Example 2 : 2,3-Dihydroxyquinoxaline The synthesis process:

[0026]

[0027] The solvent is methanol, and the reaction temperature is reflux (65°C). The reaction time was 12 hours. All the other are identical with embodiment 1. The yield was 74%.

Embodiment 3

[0028] Example 3 : 2,3-Dihydroxyquinoxaline The synthesis process:

[0029]

[0030] The solvent is ethylene glycol dimethyl ether, and the reaction temperature is reflux (85°C). The reaction time is 24 hours. All the other are identical with embodiment 1. The yield was 52%.

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Abstract

The invention relates to a synthesis method of 3-ethyl carboxylate-4-chloro imidazole [1,5-a] quinoxaline, which is mainly used for solving the technical problems of the existing scarce synthetic route, expensive reaction raw materials, difficulty in amplification, narrow application range and the like. The synthesis method comprises the following steps: heating o-phenylenediamine 1 which is a cheap and available chemical raw material and diethyl oxalate for reacting in a solvent to obtain a compound 2 which is 2,3-dihydroxyl quinoxaline; heating the compound 2 and a chloride reagent for reacting to obtain a compound 3 which is 2,3-dichloro-quinoxaline; and reacting the compound 3 with ethyl isocyanoacetate in a solvent in the presence of an alkalization reagent to obtain the final product, namely 3-ethyl carboxylate-4-chloro imidazole [1,5-a] quinoxaline. By adopting the synthetic route provided by the invention, a large quantity of the 3-ethyl carboxylate-4-chloro imidazole [1,5-a] quinoxaline can be quickly and conveniently prepared.

Description

technical field [0001] The invention relates to a method for synthesizing important pharmaceutical intermediate 3-carboxylate ethyl-4-chloroimidazo[1,5-a]quinoxaline. Background technique [0002] Imidazoquinoxaline compounds, such as imidazo[1,2-a]quinoxaline, imidazo[1,5-a]quinoxaline, 1H-imidazo[4,5-b]quinoxaline, etc. and their derivatives Compounds are an important class of pharmaceutical intermediate fragments, among which imidazo[1,5-a]quinoxaline and its derivatives are widely used and play an important role in biomedicine. It is used as the molecular core to prepare multiple compounds, all of which show good biological activities, such as GABA receptor agonist / antagonist (J. Med. Chem.: 39: 1996: 3820); cAMP and cGMP phosphoric acid Diesterase inhibitors (J. Med. Chem.: 34: 1991: 2671); A 1- and A 2a- Adenosine receptor agonist (J. Med. Chem.: 30: 1995: 133); has an effective inhibitory effect on the induced toxicity of hippocampal cells (J. Med. Chem.: 40: 1997:...

Claims

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Application Information

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IPC IPC(8): C07D487/04
Inventor 于涛张杨胡滔马汝建陈曙辉
Owner 上海药明康德新药开发有限公司
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