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Method for preparing quinoxaline compounds and benzimidazole compounds

A technology of quinoxillin and benzimidazole, which is applied in the field of preparation of pharmaceutical intermediates, can solve the problems of unobtainable raw materials, complicated operation and the like, and achieves the effects of convenient operation, high product purity and wide industrial application prospects.

Active Publication Date: 2013-06-05
特康药业集团有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to provide a preparation method of quinoxacillin compounds and benzimidazole compounds. The method has mild process conditions and a wide range of applications. The quinoxacillin compounds and benzimidazoles are synthesized in one step through one-pot reaction. The compound overcomes the shortcomings of the prior art that the raw materials are not easy to obtain and the operation is cumbersome.

Method used

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  • Method for preparing quinoxaline compounds and benzimidazole compounds
  • Method for preparing quinoxaline compounds and benzimidazole compounds
  • Method for preparing quinoxaline compounds and benzimidazole compounds

Examples

Experimental program
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Effect test

Embodiment 1

[0020] Embodiment 1 quinoxacillin compound I-a, benzimidazole compound II-a

[0021] With 58mg (0.5mmol) phenylpropadiene, 4.94mg (0.01mmol) triphenylphosphine gold chloride ((PPh) 3 AuCl), 7.8mg (0.04mmol) of silver tetrafluoroborate, 2uL (0.005mmol) of 98% concentrated sulfuric acid and 150uL (8.3mmol) of water were mixed in 1mL of dioxane, reacted at 60°C for 24 hours, and then added 37.8mg (0.35mmol) o-phenylenediamine, 9.0mg (0.1mmol) oxalic acid, reflux reaction at 80°C for 4 hours, TLC follow-up detection, after the reaction was completed, extracted with ethyl acetate (50mL×3), dried over anhydrous sodium sulfate, and filtered , concentrated, separated by silica gel column chromatography (the height of the chromatographic column is 20cm, and the diameter is 1cm; the elution flow rate is 1mL / min) (eluent: V 石油醚 :V 乙酸乙酯 =5:1), TLC (developing solvent: V 石油醚 :V 乙酸乙酯 = 5:1) Tracking detection collection R f For the eluent with a value of 0.6 to 0.65, the eluent was dis...

Embodiment 2

[0026] Embodiment 2 Quinocillin compound I-a, benzimidazole compound II-a

[0027]Dioxane was replaced by tetrahydrofuran, and other operations were the same as in Example 1 to obtain 9.53 mg of 2-methyl-3-phenylquinoxicillin (I-a), with a yield of 8.7%; 1-benzyl-2-phenyl Benzimidazole (II-a) 6.58 mg, yield 9.3%.

Embodiment 3

[0029] Dioxane was replaced with toluene, and other operations were the same as in Example 1 to obtain 20.0 mg of 2-methyl-3-phenylquinoxacillin (I-a), with a yield of 18.2%, 1-benzyl-2-phenyl Benzimidazole (II-a) 19.5 mg, yield 27.5%.

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Abstract

The invention discloses a method for preparing quinoxaline compounds shown in formula (I) and benzimidazole compounds shown in formula (II), which comprises the following steps: reacting allenic compounds shown in formula (III) in an inert organic solvent at 25-90 DEG C for 1-48 hours under the action of a catalyst, protonic acid and water; then adding oxalic acid and o-phenylenediamine, and reacting at 50-120 DEG C for 1-24 hours; and after the reaction, carrying out post treatment on the reaction liquid to obtain the quinoxaline compounds shown in formula (I) and the benzimidazole compoundsshown in formula (II), wherein the catalyst is triphenyl gold chloride and silver tetrafluoroborate; the protonic acid is concentrated sulfuric acid, and methanesulfonic acid or p-toluenesulfonic acid or trifluoroacetic acid; and the inert organic solvent is an organic solvent which can not react with the allenic compounds. By using the one-pot method to prepare the quinoxaline compounds, the invention has the advantages of mild reaction conditions, convenient operation process and high product purity.

Description

(1) Technical field [0001] The invention relates to a preparation method of a pharmaceutical intermediate, in particular to a preparation method of quinoxacillin compounds and benzimidazole compounds. (2) Background technology [0002] Quinocillin is an important nitrogen-containing heterocyclic compound with many pharmacological activities, such as antiprotozoal, antibacterial, antifungal and anticancer pharmacological activities. The method of synthesizing quinoxacillin is mainly obtained through the condensation reaction of 1,2-diketone and o-phenylenediamine (Alireza Hasaninejad, Abdolkarim Zare, Mohammad Reza Mohammadizadeh, ARKIVOC (2008), xiii, 28-35). [0003] Benzimidazole is an important nitrogen-containing heterocyclic compound. As a part of histamine side chain, the imidazole group plays a major role in the biological activity of polypeptides and proteins. The functionalized imidazole group also has many pharmacological activities, such as anti-HIV, anti-syncope...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D241/42C07D235/18
Inventor 崔冬梅庄丹闻陈颖
Owner 特康药业集团有限公司
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