Method for synthesizing amiodarone impurity G and application of amiodarone impurity G

A synthesis method and technology of amiodarone, applied in the application of amiodarone impurity G, the synthesis field of amiodarone impurity G, can solve the problems such as an undisclosed high-efficiency synthesis method of amiodarone impurity G, and achieve high purity and cost. Low, high-yield effects

Active Publication Date: 2017-05-10
成都摩尔生物医药有限公司
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Problems solved by technology

However, in the prior art, the efficient synthesi...

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  • Method for synthesizing amiodarone impurity G and application of amiodarone impurity G
  • Method for synthesizing amiodarone impurity G and application of amiodarone impurity G
  • Method for synthesizing amiodarone impurity G and application of amiodarone impurity G

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preparation example Construction

[0026] The invention provides a kind of synthetic method of amiodarone impurity G, comprising the following steps:

[0027] (1) Under the protection of an inert gas, the compound of the structure shown in formula I and n-butyllithium carry out the first reaction in the reaction medium;

[0028] (2) After the first reaction is finished, add the compound with the structure shown in formula II to the reaction liquid of the first reaction, and carry out the second reaction to obtain the compound with the structure shown in formula III, namely the amiodarone impurity G.

[0029]

[0030] Wherein, the compound of structure shown in formula I, chemical name is: 3-bromo-2-(1-methoxybutyl) benzofuran; The compound of structure shown in formula II, chemical name is: 4-(2- (Diethylamino)ethoxy)-3,5-diiodobenzoyl chloride.

[0031] It should be noted that the synthesis method provided by the present invention needs to be carried out under anhydrous conditions.

[0032] In a preferred...

Embodiment 1

[0070] Add 90mL of tetrahydrofuran and 6g of the compound of formula I to a 250mL three-necked flask, protect it under nitrogen, cool to -70°C, add 10mL of 2.5mol / L n-butyllithium solution dropwise, and ensure that the temperature is controlled less than -65°C, react at -70°C for 10 minutes after the addition is complete. Then 3 g of the compound represented by formula II and 0.2 g of anhydrous ferric chloride were added, and then returned to room temperature for 2 h of reaction.

[0071]

[0072] The reaction solution after the reaction was purified, concentrated to dryness under reduced pressure with a rotary evaporator, the pressure was set to 0.09Mpa, and the concentration temperature was 35°C. The concentrated solution was separated and purified by HPLC. The specific parameters of HPLC were set as follows:

[0073] Column: DAC 100-10 C18

[0074] Mobile phase: Phase A, 0.1% formic acid; Phase B, methanol

[0075] Flow rate: 150mL / min

[0076] Detection wavelength: 2...

Embodiment 2

[0082] Add 67mL of tetrahydrofuran and 6g of the compound of formula I to a 250mL three-necked flask, protect it under nitrogen, cool to -70°C, add 10mL of 2.5mol / L n-butyl lithium solution dropwise, and ensure that the temperature is controlled less than -65°C, react at -70°C for 10 minutes after the addition is complete. Then, 2.7 g of the compound represented by formula II and 0.1 g of anhydrous ferric chloride were added, and then returned to room temperature for 2 h of reaction.

[0083] According to the purification method provided in Example 1, the reaction solution was purified by HPLC and concentrated under reduced pressure to finally obtain 2.7 g of a light brown oily substance, namely amiodarone impurity G, with a yield of 75%.

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Abstract

The invention provides a method for synthesizing an amiodarone impurity G and application of the amiodarone impurity G, and relates to the technical field of chemical synthesis. According to the method for synthesizing the amiodarone impurity G, the amiodarone impurity G can be synthesized by one-step reaction of 3-bromo-2-(1-methoxybutyl)benzofuran and 4-(2-(diethylamino)ethoxy)-3,5-diiodobenzoyl chloride which are adopted as raw materials under protection of inert gas. The method is easy to operate and low-cost, and has certain commercial value. In addition, when the amiodarone impurity G synthesized by the method is used as an impurity reference substance, a qualified, low-cost and readily-available reference substance is provided for quality control over amiodarone, and great guiding significance is provided for safe medication.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a method for synthesizing amiodarone impurity G and the application of amiodarone impurity G. Background technique [0002] Amiodarone, also known as Amiodarone, its English name is Amiodarone. Amiodarone belongs to class III antiarrhythmic drugs, and it is suitable for atrial premature beats and premature ventricular beats when taken orally; for repeated paroxysmal supraventricular tachycardia, atrial fibrillation, atrial flutter, ventricular tachycardia and ventricular fibrillation It can prevent recurrent attacks, and also prevent pre-excitation syndrome with supraventricular arrhythmia and maintenance treatment after electrical conversion of atrial fibrillation or atrial flutter. [0003] The quality standards of amiodarone are recorded in the pharmacopoeias of many countries, and the British Pharmacopoeia clearly points out the specific structure of the impurity ...

Claims

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Application Information

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IPC IPC(8): C07D307/80G01N30/02G01N30/90
CPCC07D307/80G01N30/02G01N30/90
Inventor 郑文金田单彭捷罗焕梁彬
Owner 成都摩尔生物医药有限公司
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