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Synthetic method of drug intermediate of hemosanone, parent nucleus of hemosanone

A synthetic method, the technology of hemosanone, applied in the field of organic synthesis, can solve problems such as low efficiency and by-product pollution, and achieve the effects of low cost, simple process and high yield

Active Publication Date: 2017-08-08
广州朗启生物科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, the traditional method is not only inefficient, but also produces a large amount of by-product pollution.

Method used

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  • Synthetic method of drug intermediate of hemosanone, parent nucleus of hemosanone
  • Synthetic method of drug intermediate of hemosanone, parent nucleus of hemosanone
  • Synthetic method of drug intermediate of hemosanone, parent nucleus of hemosanone

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Experimental program
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preparation example Construction

[0030] The synthetic method of fushanone parent nucleus, the step is:

[0031] 1) In the presence of a catalyst, heat 3-bromo-4-chloroaniline and trimethyl orthoformate to fully react, cool, and then react with NH 3 Fully reacted, separated and preliminarily purified to obtain a solid crude product;

[0032] 2) In the presence of a catalyst, the solid crude product obtained in the previous step was mixed with CO, O 2 Heating for sufficient reaction, separation and purification to obtain the final product.

[0033] Preferably, in step 1), the catalyst is a protonic acid catalyst; more preferably, it is one of p-toluenesulfonic acid, solid superacid, and dodecylbenzenesulfonic acid; even more preferably, it is p-toluenesulfonic acid toluenesulfonic acid;

[0034] Preferred, NH 3 The use form is saturated methanol solution of ammonia;

[0035] Preferably, the dosage ratio of 3-bromo-4-chloroaniline, trimethyl orthoformate and saturated methanol solution of ammonia is (1-5) m...

Embodiment

[0047] The synthetic method of fushanone parent nucleus, the step is:

[0048] 1. Preparation of Compound 2

[0049] 3-Bromo-4-chloroaniline (compound 1, 0.2 g) was heated and mixed with trimethyl orthoformate (5 mL), a catalytic amount of p-toluenesulfonic acid (2 mg) was added, heated to reflux under stirring, and the Analysis (TLC) followed the reaction and detected by ultraviolet light until compound 1 disappeared completely. After cooling to room temperature, a saturated methanol solution of ammonia (2 mL) was added and stirred at room temperature for 10 hours. Methanol and remaining trimethyl orthoformate were distilled off to obtain a crude compound 2 (0.22 g) as a solid. Wash once with water (10 mL) and air dry. The product was directly used in the next reaction without further purification.

[0050] 2. Synthesis of hemosanone mother nucleus

[0051] The above reaction solid crude product (0.22 g) was mixed with glacial acetic acid (10 mL) and palladium acetate (1...

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Abstract

The invention discloses a drug intermediate of halofuginone and a synthesis method of a halofuginone parent nucleus. The structural formula of the intermediate is disclosed in the specification. The synthesis method of the halofuginone parent nucleus is characterized by comprising the following steps: 1) in the presence of a catalyst, heating 3-bromo-4-chloroaniline and trimethyl orthoformate to sufficiently react, cooling, sufficiently reacting with NH3, separating, and carrying out primary purification to obtain a solid crude product; and 2) in the presence of a catalyst, sufficiently heating the obtained solid, acetic acid, CO and O2 to react, separating and purifying to obtain the end product. The synthesis method is a two-step process, and has the advantages of simple technique, environment friendliness, high yield and very low cost since the raw materials are accessible 3-bromo-4-chloroaniline and trimethyl orthoformate.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a drug intermediate of hemosanone and a synthesis method of hemosanone mother nucleus. Background technique [0002] The synthesis of the parent nucleus of hemosanone is the most important problem in the production process of hemosanone. At present, there are 6 patents related to the synthesis of hiradhenone, CN 2013 103467449, CN 2013 103275063, CN 2011 101987843, CN 2010101648942, CN 2005 1651428, WO 2001034149 A1 20010517. Chloroacetaldehyde is reacted with hydroxylamine, hydrolyzed by sulfuric acid and cyclized, sulfuric acid chloride is chlorinated to introduce chlorine atoms, hydrogen peroxide is oxidized and then reacted with formamide to obtain the final compound nucleus. Not only are there many reaction steps, but more importantly, the secondary product obtained by the cyclization reaction is the desired target product. Therefore, the traditional method is not only ine...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C257/12C07D239/90
Inventor 邱发洋邱俊郑云杰王冰洋钟娟汪清国
Owner 广州朗启生物科技有限公司
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