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Synthesis method of 1-(4-aminopyridine-2-yl)ethanone

A synthesis method and aminopyridine technology, applied in the direction of organic chemistry, etc., can solve the problems of harsh equipment drying and reaction temperature control, poor economic benefit and environmental impact, and complicated post-processing process, and achieve easy operation of post-processing and purification. , risk reduction, mild reaction conditions

Inactive Publication Date: 2019-11-05
上海毕得医药科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Under the protection of the amino group, the cyano group is converted into an acetyl group with a methyl Grignard reagent. Due to the use of the Grignard reagent, the production process has strict requirements on the reaction conditions such as solvent moisture, equipment drying and reaction temperature control, and the reaction yield is low. Post-treatment The process is cumbersome, and the economic benefit and environmental impact are not good

Method used

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  • Synthesis method of 1-(4-aminopyridine-2-yl)ethanone
  • Synthesis method of 1-(4-aminopyridine-2-yl)ethanone
  • Synthesis method of 1-(4-aminopyridine-2-yl)ethanone

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Embodiment 1

[0026]

[0027] ① Mix 25g (1eq) 2-chloro-4-nitropyridine, 65g (1.15eq) tributyl (1-ethoxyethylene) tin and 3g (0.03eq) Pd (PPh 3 ) 2 Cl 2 Add 300ml of DMF, under argon protection, react at 85°C for 3h, pour 1L of ice water into it at room temperature, extract with EA, spin dry, add 300ml of 2M hydrochloric acid aqueous solution, stir the whole system at room temperature overnight, extract with EA, mix the sample and pass through the column to purify the compound II 26g, yield 99%.

[0028] ②Add 26g of compound II to 200ml of methanol, add 2g of Pd / C, and react overnight with hydrogen gas; TLC, the reaction is complete, spin dry and filter with PE beating to obtain 19g of the target product 1-(4-aminopyridin-2-yl)ethanone , yield 89.5%, H NMR spectrum such as figure 1 shown.

Embodiment 2

[0030]

[0031] ① Mix 5g (1eq) 2-chloro-4-nitropyridine, 12.5g (1.1eq) tributyl (1-ethoxyethylene) tin and 0.7g (0.03eq) Pd (PPh 3 ) 2 Cl 2 Add 50ml of NMP, under argon protection, react at 90°C for 3h, drop to room temperature and pour 200ml of ice water, extract with EA, spin dry, add 50ml of 2M hydrochloric acid aqueous solution, stir overnight at room temperature, extract with EA, mix the sample and pass through the column to obtain 23g of compound , yield 58%.

[0032] ②Add 3g of compound 2 to 30ml of methanol, add 0.3g of Pd / C, and react overnight with hydrogen gas, TLC, the reaction is complete, spin dry, and beat with PE to obtain 2.1g of 1-(4-aminopyridin-2-yl)ethanone, Yield 85%.

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Abstract

The invention discloses a synthesis method of 1-(4-aminopyridine-2-yl)ethanone. 2-chloro-4-nitropyridine is taken as a raw material, tributyl(1-ethoxyethylene)tin is subjected to acetyl coupling and reduction nitro reaction. The method includes the following steps that 2-chloro-4-nitropyridine, tributyl(1-ethoxyethylene)tin and Pd(PPh3)2Cl2 are added into a solvent a, reaction lasts for 3 hours at75-100 DEG C under protection of argon gas or nitrogen gas, then the temperature is reduced to room temperature, ice water is added, EA extraction is conducted, spin-drying is performed, a dilute hydrochloric acid solution is added, stirring is conducted at room temperature, after the solution is placed over night, EA extraction and purification are conducted in sequence, the obtained compound isadded into a solvent b, then a Pd / C catalyst is added, H2 is introduced for reduction, spin-drying and PE beating are performed, and 1-(4-aminopyridine-2-yl)ethanone is obtained. According to the synthesis method, raw materials are easy to obtain, the reaction condition is mild, the yield is high, after-treatment and purification are easy to operate, and scale production can be achieved.

Description

technical field [0001] The invention belongs to the field of organic synthesis of pharmaceutical intermediates, in particular to a method for synthesizing 1-(4-aminopyridin-2-yl)ethanone. Background technique [0002] At present, pyridine compounds have been studied for the prevention and treatment of atherosclerosis, and are also used as substrates for the preparation of antiviral drugs, wherein the synthetic method of 1-(4-aminopyridin-2-yl)ethanone has been According to reports, the synthetic route is shown in the following formula (1): [0003] [0004] Under the protection of the amino group, the cyano group is converted into an acetyl group with a methyl Grignard reagent. Due to the use of the Grignard reagent, the production process has strict requirements on the reaction conditions such as solvent moisture, equipment drying and reaction temperature control, and the reaction yield is low. Post-treatment The process is cumbersome, and the economic benefit and envir...

Claims

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Application Information

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IPC IPC(8): C07D213/73
CPCC07D213/73
Inventor 陈华郦荣浩
Owner 上海毕得医药科技股份有限公司
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