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Synthesis method of imidazo[1,2-alpha]pyridyl-3-formic acid

A synthesis method, 2-a technology, applied in organic chemistry and other directions, can solve the problems of many by-products, complicated operation, difficult to purify and purify, etc., and achieve the effects of stable product quality, mild reaction conditions and simple post-processing.

Inactive Publication Date: 2014-08-06
SHANDONG YOUBANG BIOCHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This technology makes it easier for people who want something that's expensive or difficult to make at home compared with those trying to get things done quickly on their own. It also has several advantages such as being able to react very well under gentle conditions without getting damaged during production process, operating easily over time, controlling its output effectively, making sure products are free from impurities like bubbles, moisture, etc., which can affect them negatively impacted by factors like temperature changes.

Problems solved by technology

This technical problem addressed in this patented text relates to improving the process for producing certain types of compounds with specific substituents on their molecular structure through reducing impurities or unwanted reactions during various stages involved in the manufacturing processes.

Method used

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  • Synthesis method of imidazo[1,2-alpha]pyridyl-3-formic acid

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Experimental program
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Embodiment 1

[0027] 80mL (71.7g) of N,N-dimethylformamide dimethyl acetal is both solvent and reaction raw material, react with 2-aminopyridine (18.8g, 200mmol) at 40°C for 5 hours, and the reaction is completed to obtain N, N-dimethyl-N'-2-pyridylformamidine intermediate, rotary evaporation to remove excess N,N-dimethylformamide dimethyl acetal, add 120 mL (114g) N,N-dimethyl Formamide (DMF), NaHCO 3 (25.2g, 300mmol) and ethyl bromoacetate (50.1g, 300mmol), react at 50°C for 10 hours, after the reaction is completed, cool to room temperature, add 600 mL of water and 200 mL of ethyl acetate for extraction, separate the organic phase and the aqueous phase Extract with ethyl acetate (3×200 mL), combine the organic phases, wash with water (2×150 mL), wash with 200 mL saturated brine, anhydrous Na 2 SO 4 Dry, filter, and concentrate the filtrate to obtain the crude product of ethyl imidazo[1,2-a]pyridine-3-carboxylate, which is recrystallized from a mixed solution of n-hexane:ethyl acetate=1...

Embodiment 2

[0030] 80mL (71.7g) of N,N-dimethylformamide dimethyl acetal is both solvent and reaction raw material, react with 2-aminopyridine (18.8g, 200mmol) at 40°C for 5 hours, and the reaction is completed to obtain N, N-dimethyl-N'-2-pyridylformamidine intermediate, rotary evaporation to remove excess N,N-dimethylformamide dimethyl acetal, add 120 mL (125 g) of dioxane, K 2 CO 3 (20.8g, 150mmol) and ethyl bromoacetate (50.1g, 300mmol), react at 80°C for 10 hours, after the reaction is completed, cool to room temperature, add 600 mL of water and 200 mL of ethyl acetate for extraction, separate the organic phase and the aqueous phase Extract with ethyl acetate (3×200 mL), combine the organic phases, wash with water (2×150 mL), wash with 200 mL saturated brine, anhydrous Na 2 SO 4 Dry, filter, and concentrate the filtrate to obtain the crude product of ethyl imidazo[1,2-a]pyridine 3-carboxylate, which is recrystallized from a mixed solution of n-hexane:ethyl acetate=1:1 (volume ratio...

Embodiment 3

[0033] N,N-Dimethylformamide dimethyl acetal (80mL) is both a solvent and a reaction raw material, reacted with 2-aminopyridine (18.8g, 200mmol) at 60°C for 5 hours, and the reaction was completed to obtain N,N- Dimethyl-N'-2-pyridylformamidine intermediate, remove excess N,N-dimethylformamide dimethyl acetal by rotary evaporation, add 120 mL (103g) toluene, triethylamine (30.3g , 300mmol) and ethyl bromoacetate (50.1g, 300mmol), reacted at 100°C for 8 hours, after the reaction was completed, cooled to room temperature, added 600 mL of water and 200 mL of ethyl acetate for extraction, separated the organic phase, and used acetic acid for the aqueous phase Extract with ethyl ester (3×200 mL), combine the organic phases, wash with water (2×150 mL), wash with 200 mL saturated brine, anhydrous Na 2 SO 4 Dry, filter, and concentrate the filtrate to obtain the crude product of ethyl imidazo[1,2-a]pyridine-3-carboxylate, which is recrystallized from a mixed solution of n-hexane:ethy...

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Abstract

The invention belongs to the field of organic synthesis, and particularly relates to a synthesis method of imidazo[1,2-alpha]pyridyl-3-formic acid. The method comprises the following steps: reacting N,N-dimethylformamidodimethyl acetal with 2-aminopyridine at 40-100 DEG C for 2-8 hours to obtain an N,N-dimethyl-N'-2-pyridylformamidine intermediate, reacting the intermediate with ethyl bromoacetate at 50-160 DEG C, and recrystallizing to obtain a pure product; carrying out hydrolysis reaction on ethyl imidazo[1,2-alpha]pyridyl-3-formate in a certain solvent for 1-5 hours; and after the reaction finishes, neutralizing with hydrochloric acid, filtering, washing with water, and drying to directly obtain the imidazo[1,2-alpha]pyridyl-3-formic acid pure product. The method has the advantages of accessible reaction raw materials, reasonable price, mild reaction conditions and simple after-treatment, and is easy to operate and control; and the product has the advantages of stable quality and high purity.

Description

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Claims

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Application Information

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Owner SHANDONG YOUBANG BIOCHEM TECH
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