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Synthetic method of 6-chlorine-8-carboxyl imidazo [1,2-a] pyridine

The technology of a carboxyimidazole and a synthetic method, which is applied in the synthesis field of 6-chloro-8-carboxyimidazo[1,2-a]pyridine, can solve the problems such as lack of literature and patent reports, high market price, difficult synthesis, etc. Effects that are easy to generalize, easy to control, and easy to post-process

Inactive Publication Date: 2015-06-24
SHANDONG YOUBANG BIOCHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This product is a novel pharmaceutical intermediate with great medical value, but its synthesis is difficult, the market price is expensive, and there is a lack of literature and related patent reports

Method used

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  • Synthetic method of 6-chlorine-8-carboxyl imidazo [1,2-a] pyridine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Add 17.25g of dioxane in a 100ml round-bottom single-necked flask, insert a thermometer and start a magnetic stirrer, and add 17.25g of 2-aminonicotinic acid, add 10.01g of N-chlorosuccinimide, and react in The reaction was carried out at 15°C for 6 hours, and the reaction was confirmed to be complete by TLC and GC. Without purification, 9.81 g of 40% aqueous solution of chloroacetaldehyde was added and reacted at 70° C. for 10 hours while stirring. TLC and GC confirmed the completion of the reaction. After the reaction, filter with suction, dissolve in ethanol, add 5.00g of sodium hydroxide to it, neutralize, filter with suction, recrystallize with a mixed solution of n-hexane and ethyl acetate with a volume ratio of 3:1, filter with suction, wash with water, and dry Dry directly to obtain pure 6-chloro-8-carboxyimidazo[1,2-a]pyridine. After drying, 10.41 g of pure product was obtained with a yield of 53%. 1 HNMR (400MHz, CDCl 3 ): 11.2(s,1H), 8.67(s,1H), 7.72(d,J=...

Embodiment 2

[0020] Add 17.25g of acetonitrile into a 100ml round-bottom single-necked flask, insert a thermometer and start a magnetic stirrer, and add 17.25g of 2-aminonicotinic acid, add 10.01g of N-chlorosuccinimide, and react at 15°C After 7 hours of reaction, TLC and GC confirmed that the reaction was complete. Without purification, 9.81 g of 40% aqueous solution of chloroacetaldehyde was added, and the mixture was reacted at 70° C. for 12 hours while stirring. TLC and GC confirmed the completion of the reaction. After the reaction, filter with suction, dissolve in ethanol, add 5.00g of sodium hydroxide to it, neutralize, filter with suction, recrystallize with a mixed solution of n-hexane and ethyl acetate with a volume ratio of 3:1, filter with suction, wash with water, and dry Dry directly to obtain pure 6-chloro-8-carboxyimidazo[1,2-a]pyridine. After drying, 9.432g of pure product was obtained, with a yield of 48%. 1HNMR(400MHz,,CDCl3):11.2(s,1H),8.67(s,1H),7.72(d,J=8.0Hz,1...

Embodiment 3

[0022] Add 17.25g of N,N-dimethylacetamide to a 100ml round-bottom single-necked flask, insert a thermometer to start a magnetic stirrer, and add 17.25g of 2-aminonicotinic acid, add 10.01g of N-chlorosuccinyl imine, the reaction was carried out at 15°C for 8 hours, and the reaction was complete as determined by TLC and GC. Without purification, 9.81 g of 40% aqueous solution of chloroacetaldehyde was added, and the mixture was reacted at 70° C. for 11 hours while stirring. TLC and GC confirmed the completion of the reaction. After the reaction, filter with suction, dissolve in ethanol, add 5.00g of sodium hydroxide to it, neutralize, filter with suction, recrystallize with a mixed solution of n-hexane and ethyl acetate with a volume ratio of 3:1, filter with suction, wash with water, and dry Dry directly to obtain pure 6-chloro-8-carboxyimidazo[1,2-a]pyridine. After drying, 8.253 g of pure product was obtained, with a yield of 42%.

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Abstract

The invention relates to a synthetic method of 6-chlorine-8-carboxyl imidazo [1,2-a] pyridine. The method comprises the following steps: performing reaction on 2-aminonicotinic acid and chlorosuccinimide at the temperature of 0-100 DEG C to prepare a 2-amino-5 chloronicotinic acid intermediate; without needing purification of the intermediate, performing reaction on the intermediate and chloroacetaldehyde at the temperature of 70-160 DEG C in a certain solvent; by the end of reaction, performing suction filtration, dissolving in the certain solvent, neutralizing under an alkali function, performing suction filtration, recrystallizing, performing suction filtration again, washing and drying to directly obtain a 6-chlorine-8-carboxyl imidazo [1,2-a] pyridine pure product. The raw materials are easily available and reasonable in price; meanwhile, in the preparation and reaction process, heavy metals and corrosive gas are not used, and the reaction is mild; a special requirement on reaction equipment is not required, and the 6-chlorine-8-carboxyl imidazo [1,2-a] pyridine can be produced by using common corrosion-resistant equipment; and in addition, the synthetic method is moderate in reaction conditions.

Description

(1) Technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to a synthesis method of 6-chloro-8-carboxyimidazo[1,2-a]pyridine. (2) Background technology [0002] 6-Chloro-8-carboxyimidazo[1,2-a]pyridine is an important intermediate in organic synthesis, mainly used in pharmaceutical intermediates, organic synthesis, organic solvents, and can also be used in dye production, pesticide production and spices, etc. aspect. This product is a novel pharmaceutical intermediate with great medical value, but its synthesis is difficult, the market price is expensive, and there is a lack of literature and related patent reports. (3) Contents of the invention [0003] The problem to be solved in the present invention is to provide a synthetic method of 6-chloro-8-carboxyimidazo[1,2-a]pyridine that is simple and reasonable in process, low in cost, high in product purity and suitable for industrialization in view of the prior art . ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 来新胜韩猛曹惊涛
Owner SHANDONG YOUBANG BIOCHEM TECH
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