Preparation technology for 1-(3-amino-4-pyridyl) aceton

A preparation process and aminopyridine technology are applied in the field of preparation technology of 1-ethyl ketone, which can solve the problems of high price and high production cost, and achieve the effects of cheap raw materials, mild and easy-to-control operation conditions, and favorable industrial application.

Inactive Publication Date: 2017-11-24
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The technical problem to be solved in the present invention is: provide a kind of preparation technology of 1-(3-amino-4-pyridyl) ethyl ketone, to solve prior art in the preparation of 1-(3-amino-4-pyridyl) ethyl ketone When using ketones, the raw materials and reagents are expensive, and the production cost is high.

Method used

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  • Preparation technology for 1-(3-amino-4-pyridyl) aceton

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] A. Preparation of 3-pivalamidopyridine

[0013] In a three-necked flask, 3-aminopyridine (20.0g, 212.5mmol), 4-dimethylaminopyridine (4-DMAP) (0.3g, 2.1mmol) and pyridine (33.6g, 425.0mmol) were dissolved in anhydrous di In methyl chloride (200mL), pivaloyl chloride (28.2g, 233.7mmol) was slowly added dropwise under ice-cooling, and reacted at 0°C for 2h. After the reaction was completed, the reaction solution was poured into ice water, quenched with 1N hydrochloric acid, extracted with dichloromethane (250mL×3), the organic phase was collected, washed with saturated brine (200mL×1), and the solvent was evaporated under reduced pressure to obtain 3- 36.2 g of pivalamidopyridine, yield 95.5%.

[0014] B. Preparation of N-(4-ethylpyridin-3-yl)trimethylacetamide

[0015] In a three-necked flask, 3-pivalamidopyridine (20.0 g, 112.2 mmol) was dissolved in anhydrous tetrahydrofuran (200 mL), cooled to -78°C under nitrogen protection, and n-butyllithium (17.3 g, 269.3mmol),...

Embodiment 2

[0020] A. Preparation of 3-pivalamidopyridine

[0021] In a three-necked flask, 3-aminopyridine (20.0g, 212.5mmol), 4-dimethylaminopyridine (4-DMAP) (0.3g, 2.1mmol) and pyridine (33.6g, 425.0mmol) were dissolved in anhydrous di To methyl chloride (200 mL), slowly add pivaloyl chloride (25.6 g, 212.5 mmol) dropwise under ice-cooling, and react at 30°C for 1 h after the drop is complete. After the reaction was completed, the reaction solution was poured into ice water, quenched with 1N hydrochloric acid, extracted with dichloromethane (250mL×3), the organic phase was collected, washed with saturated brine (200mL×1), and the solvent was evaporated under reduced pressure to obtain 3- 33.8 g of pivalamidopyridine, yield 89.2%.

[0022] B. Preparation of N-(4-ethylpyridin-3-yl)trimethylacetamide

[0023] In a three-necked flask, 3-pivalamidopyridine (20.0 g, 112.2 mmol) was dissolved in anhydrous tetrahydrofuran (200 mL), cooled to -78°C under nitrogen protection, and n-butyllithi...

Embodiment 3

[0028] A. Preparation of 3-pivalamidopyridine

[0029] In a three-necked flask, 3-aminopyridine (20.0g, 212.5mmol), 4-dimethylaminopyridine (4-DMAP) (2.6g, 21.2mmol) and pyridine (168.1g, 2124.9mmol) were dissolved in anhydrous di Pivaloyl chloride (51.3 g, 425.0 mmol) was slowly added dropwise to methyl chloride (200 mL) in an ice bath, and reacted at -10°C for 2 h. After the reaction was completed, the reaction solution was poured into ice water, quenched with 1N hydrochloric acid, extracted with dichloromethane (250mL×3), the organic phase was collected, washed with saturated brine (200mL×1), and the solvent was evaporated under reduced pressure to obtain 3- 35.1 g of pivalamidopyridine, yield 92.5%.

[0030] B. Preparation of N-(4-ethylpyridin-3-yl)trimethylacetamide

[0031] In a three-necked flask, 3-pivalamidopyridine (20.0 g, 112.2 mmol) was dissolved in anhydrous tetrahydrofuran (200 mL), cooled to -78°C under nitrogen protection, and n-butyllithium (21.6 g, 336.6m...

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Abstract

The invention discloses a preparation technology for 1-(3-amino-4-pyridyl) aceton. The preparation technology is characterized by comprising the following steps: (1) by taking 3-aminopyridine as a raw material, participating into amidation reaction, thereby generating 3-teramidyl pyridine; (2) generating N-(4-aceton pyridine-3-group) trimethyl acetamide through the substitution reaction of the 3-teramidyl pyridine; and (3) hydrolyzing the N-(4-aceton pyridine-3-group) trimethyl acetamide, thereby acquiring the target product 1-(3-amino-4-pyridyl) aceton. The raw materials in process route are low in cost and easily acquired, the operation condition is mild and easily controlled and the preparation technology is beneficial to the industrial application.

Description

technical field [0001] The invention relates to a preparation process of 1-(3-amino-4-pyridyl)ethanone. It belongs to the fields of fine chemicals, pharmaceutical intermediates and materials. Background technique [0002] Compounds containing pyridine rings not only play an important role in the production of medicines, pesticides, dyes, etc., but are also one of the most common intermediates in many organic synthesis. 1-(3-amino-4-pyridyl)ethanone, as one of them, is a synthetic TGFβR antagonist, GSK-3 inhibitor, KCNQ2 / 3 regulator, Wnt inhibitor, pyridopyridine antitumor drug or An important intermediate for PET radioligands of translocated proteins. [0003] At present, there are mainly the following types of synthetic techniques for 1-(3-amino-4-pyridyl)ethanone: the route reported by Bakke, J.M. et al. uses 3-nitropyridine-4-carboxylic acid as a raw material to synthesize the target compound. The route reported by Luzzio, Michael Joseph, etc. uses 3-nitro-4-pyridinald...

Claims

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Application Information

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IPC IPC(8): C07D213/73
CPCC07D213/73
Inventor 刘力黄筑艳乐意
Owner GUIZHOU UNIV
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