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Method for synthesizing benzydamine hydrochloride impurity B

A technology of benzydamine hydrochloride and impurity, which is applied in the field of synthesizing benzydamine hydrochloride impurity B, can solve problems such as not existing, and achieve the effect of simple reaction route and strong practical value

Pending Publication Date: 2021-07-27
LONGXINING SHANGHAI PHARMA TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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  • Method for synthesizing benzydamine hydrochloride impurity B
  • Method for synthesizing benzydamine hydrochloride impurity B
  • Method for synthesizing benzydamine hydrochloride impurity B

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Embodiment 1

[0045] Following synthetic route, present embodiment provides the method for synthetic benzydamine hydrochloride impurity B, and it comprises the steps:

[0046]

[0047] Step 1, raw material 1-2-amino-5-benzylbenzoic acid methyl ester (50mg, 0.2mmol), lithium hydroxide hydrate (26mg, 0.6mmol), 1,4 dioxane (3ml), water ( 5ml) were sequentially added into a three-neck flask, heated to reflux for 1 hour, extracted with EA and spin-dried to obtain intermediate product 2 (40mg, yield: 85%).

[0048] 1 H NMR(300MHz,DMSO)δ8.58(s,1H),7.51(d,J=2.0Hz,1H),7.33–7.12(m,5H),7.08(d,J=8.4Hz,1H),6.65 (d,J=8.4Hz,1H),3.76(s,2H).

[0049] Step 2, the intermediate product 2 (250mg, 1.036mmol) was added to 2ml of hydrochloric acid solution, the temperature was lowered to 0°C, and NaNO was added dropwise 2 (71.5mg, 1.036mmol) in water, then stirred at 0°C for 0.5 hours, SnCl 2 (701mg, 3.1mmol) hydrochloric acid solution was added dropwise to the above solution, then reacted overnight at room...

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Abstract

The invention provides a method for synthesizing benzydamine hydrochloride impurity B. The method comprises the following steps: hydrolyzing methyl ester in a molecule by taking 2-amino-5-benzyl methyl benzoate as a starting raw material, converting amino into hydrazine through diazotization, and cyclizing carboxyl and hydrazino in the molecule by using hydrochloric acid to obtain a benzopyrazole derivative; and respectively carrying out alkylation reaction on nitrogen atoms and oxygen atoms to finally obtain the benzydamine hydrochloride impurity B. According to the method provided by the invention, 2-amino-5-benzyl methyl benzoate is taken as a starting material, a final target product is obtained through five-step reaction, and the whole reaction route is simple and efficient and has very high practical value; and the content of the impurity in the production process is very low, so that compared with a scheme of directly extracting the impurity from a reaction solution, the synthesis scheme is more convenient and economical, and the blank that the compound is not reported in literatures so far is filled up.

Description

technical field [0001] The invention relates to the technical field of pharmaceutical synthesis, in particular to a method for synthesizing benzydamine hydrochloride impurity B. Background technique [0002] Benzydamine Hydrochloride (Benzydamine Hydrochloride), also known as Xiaoyanling or Yantongjing, chemical name is 1-benzyl-3-[3-(dimethylamino)propoxy]-1H-indazole hydrochloride, which is a local Non-steroidal anti-inflammatory drug with local anesthetic and analgesic properties, used for pain relief and anti-inflammatory treatment of inflammatory conditions of the mouth and throat, and can be combined with antibiotics or sulfonamides for better efficacy, so it needs to be strictly controlled for quality . [0003] Benzydamine hydrochloride impurity B (following formula I) is the impurity that can inevitably produce in the production benzydamine hydrochloride process, and content is lower, thereby compares with the scheme of directly extracting impurity from reaction so...

Claims

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Application Information

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IPC IPC(8): C07D231/56
CPCC07D231/56
Inventor 闫强朱宁李春成
Owner LONGXINING SHANGHAI PHARMA TECH CO LTD
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