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Synthetic method of 6-chloroimidazo [1, 2-b]pyridazine-3-formic acid

A synthesis method and chloroimidazole technology are applied in the field of synthesis of 6-chloroimidazo[1,2-b]pyridazine-3-carboxylic acid, and can solve the problems of high raw material cost, high impurity content, intense reaction and the like, and achieve The effect of stable product quality, simple post-processing and easy operation

Inactive Publication Date: 2017-06-13
陕西友帮生物医药科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The existing 6-chloroimidazo[1,2-b]pyridazine-3-carboxylic acid preparation process is cumbersome, the reaction is intense, the product has high impurity content, low yield, long reaction time and high raw material cost, which is not conducive to the competitiveness of enterprises

Method used

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  • Synthetic method of 6-chloroimidazo [1, 2-b]pyridazine-3-formic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Add 3-amino-6-chloropyridazine (12.96g, 100mmol) and N,N-dimethylformamide dimethyl acetal (35.75g, 300mmol) into a 250ml three-neck round bottom flask and react at 80°C for 4 hours. TLC detects that the reaction is complete, and [2-(6-chloro-3-pyridazinyl)-2-azavinyl] dimethylamine intermediate is obtained, and the excess N,N-dimethylformamide di Methyl acetal. Pour the rotary evaporated intermediate into a 500ml three-neck flask, add 65ml N,N-dimethylformamide (DMF), sodium bicarbonate (21g, 250mmol), ethyl bromoacetate (41.75g, 250mmol) to it , react at 90°C for 12h, after the reaction is completed, cool to room temperature, add 200ml of water, add ethyl acetate (3×150ml), combine the organic phases, wash with water (3×100ml), and then wash with 150ml of saturated saline, anhydrous Dry over sodium sulfate, filter, and concentrate the filtrate to obtain crude ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate, which is recrystallized from a mixed solvent of ethyl a...

Embodiment 2

[0031] Add 3-amino-6-chloropyridazine (12.96g, 100mmol) and N,N-dimethylformamide dimethyl acetal (35.75g, 300mmol) into a 250ml three-neck round bottom flask and react at 80°C for 4 hours. TLC detects that the reaction is complete, and [2-(6-chloro-3-pyridazinyl)-2-azavinyl] dimethylamine intermediate is obtained, and the excess N,N-dimethylformamide di Methyl acetal. Pour the rotary evaporated intermediate into a 500ml three-neck flask, add 65ml of acetonitrile, sodium bicarbonate (21g, 250mmol), ethyl bromoacetate (41.75g, 250mmol), and react at 90°C for 12h. After the reaction is complete, cool to At room temperature, add 200ml of water, then add ethyl acetate (3×150ml), combine the organic phases, wash with water (3×100ml), then wash with 150ml of saturated brine, dry over anhydrous sodium sulfate, filter, and concentrate the filtrate to obtain 6- Cloimidazo[1,2-b]pyridazine-3-carboxylic acid ethyl ester crude product, the crude product was recrystallized in a mixed solv...

Embodiment 3

[0034] Add 3-amino-6-chloropyridazine (12.96g, 100mmol) and N,N-dimethylformamide dimethyl acetal (35.75g, 300mmol) into a 250ml three-neck round bottom flask and react at 80°C for 4 hours. TLC detects that the reaction is complete, and [2-(6-chloro-3-pyridazinyl)-2-azavinyl] dimethylamine intermediate is obtained, and the excess N,N-dimethylformamide di Methyl acetal. Pour the rotary evaporated intermediate into a 500ml three-neck flask, add 65ml N,N-dimethylacetamide (DMAC), sodium bicarbonate (21g, 250mmol), ethyl bromoacetate (41.75g, 250mmol) to it , react at 90°C for 12h, after the reaction is completed, cool to room temperature, add 200ml of water, add ethyl acetate (3×150ml), combine the organic phases, wash with water (3×100ml), and then wash with 150ml of saturated saline, anhydrous Dry over sodium sulfate, filter, and concentrate the filtrate to obtain crude ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate, which is recrystallized from a mixed solvent of ethyl ...

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Abstract

The invention relates to a synthetic method of 6-chloroimidazo [1, 2-b]pyridazine-3-formic acid. The synthetic method comprises the steps of reacting N,N-dimethylformamide dimethyl acetal and 3-amino-6-chloropyridazine at the temperature of 40 to 120 DEG C to obtain an intermediate; under an alkali action, reacting at the temperature of 65 to 140 DEG C, and carrying out rotary evaporation and concentration to obtain a 6-chloroimidazo [1,2-b]pyridazine-3-formic acid ethyl ester crude product; recrystallizing the crude product to obtain a pure product; under an alkali action, carrying out hydrolysis reaction in a certain solvent, finishing reaction, neutralizing through hydrochloric acid, carrying out suction filtration, and washing drying to obtain a 6-chloroimidazo [1, 2-b]pyridazine-3-formic acid pure product. The synthetic method provided by the invention is adopted for preparing the 6-chloroimidazo [1, 2-b]pyridazine-3-formic acid, so that the reaction raw materials can be obtained easily, the method is easy to operate and control and simple in aftertreatment, and the product has stable quality and high purity.

Description

[0001] (1) Technical field [0002] The invention belongs to the field of organic synthesis, and in particular relates to a synthesis method of 6-chloroimidazo[1,2-b]pyridazine-3-carboxylic acid. [0003] (2) Background technology [0004] 6-Chlorimidazo[1,2-b]pyridazine-3-carboxylic acid is an important intermediate in organic synthesis, mainly used in pharmaceutical intermediates, organic synthesis, and can also be used in dye production, pesticide production and spices. The existing 6-chloroimidazo[1,2-b]pyridazine-3-carboxylic acid has a cumbersome preparation process, intense reaction, high impurity content in the product, low yield, long reaction time and high raw material cost, which is not conducive to the competitiveness of enterprises. [0005] (3) Contents of the invention [0006] The problem to be solved in the present invention is to provide a 6-chloroimidazo[1,2-b]pyridazine-3- Synthesis of formic acid. [0007] The present invention is achieved through the fo...

Claims

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Application Information

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IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 谈平忠耿宣平程伟来新胜来超来子腾
Owner 陕西友帮生物医药科技有限公司
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