Synthesis method of 3-aminopyridine formaldehyde

A technology of aminopyridinecarboxaldehyde and synthesis method, applied in the field of pharmaceutical intermediate synthesis, can solve the problems of high toxicity of reaction reagents, expensive catalysts, troublesome post-processing, etc., and achieves convenient operation and post-processing, easy to enlarge, and low cost of raw materials. Effect

Inactive Publication Date: 2021-02-19
SUZHOU KANGRUN PHARMA
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Problems solved by technology

[0005] The purpose of the present invention is to provide a synthetic method of 3-aminopyridinecarbaldehyde, which overcomes the shortcomings of the existing synthetic methods, such as expensive catalyst, high toxicity of reaction reagents, cumbersome post-processing, difficulty in scaling up, high cost, etc.

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  • Synthesis method of 3-aminopyridine formaldehyde

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Embodiment Construction

[0024] The present invention will be further described below in conjunction with specific examples, but the examples are only exemplary and do not constitute any limitation to the scope of the present invention. Those skilled in the art should understand that the details and forms of the technical solutions of the present invention can be modified or replaced without departing from the spirit and scope of the present invention, but these modifications and replacements all fall within the protection scope of the present invention.

[0025] In the present invention, the synthetic technique of 3-aminopyridine formaldehyde is to use 2-bromonicotinic acid as raw material to carry out curtius rearrangement reaction to obtain (2-bromopyridin-3-yl) tert-butyl carbamate, and carry out Grignard reaction to obtain (2-methyl Acylpyridin-3-yl) tert-butyl carbamate, and finally hydrolyzed to give 3-aminopyridinecarbaldehyde. The reaction formula is as follows:

[0026] .

[0027] The sp...

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Abstract

The invention discloses a synthesis method of 3-aminopyridine formaldehyde, which comprises the following steps of: carrying out a cutius rearrangement reaction on 2-bromonicotinic acid serving as a raw material to obtain tert-butyl (2-bromopyridine-3-yl) carbamate, carrying out a Grignard reaction to obtain tert-butyl (2-formyl pyridine-3-yl) carbamate, and finally carrying out a hydrolysis reaction to obtain 3-aminopyridine formaldehyde. The synthesis method overcomes the defects of expensive raw materials, low yield, use of microwave reaction and other conditions, difficulty in amplification and the like in the existing synthesis process, and has the advantages of simple synthesis route, reasonable process selection, low raw material cost, simple and easily available raw materials, convenience in operation and post-treatment, high total yield, no use of highly toxic reagents, easiness in amplification, and realization of mass production.

Description

technical field [0001] The invention belongs to the technical field of synthesis of pharmaceutical intermediates, and in particular relates to a synthesis method of 3-aminopyridine formaldehyde. Background technique [0002] 3-Aminopyridinecarbaldehyde is a key pharmaceutical intermediate. As one of aromatic heterocycles, pyridine plays a very important role in drug design. Pyridine is often used to replace benzene rings in drug design, which has a positive impact on the effective conformation of ligands or favorable electrostatic interactions, or is beneficial to The hydrogen bonding required for activity is formed between the ligand and the receptor, thereby optimizing the biochemical activity, cellular activity, and target selectivity of the compound, and may even change the pharmacological function, so 3-aminopyridinecarbaldehyde is widely used. For example, Cushing T D and others have developed a new type of heterocyclic compound as a selective inhibitor of phosphatidy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/73
CPCC07D213/73
Inventor 晋浩文徐卫良徐炜政
Owner SUZHOU KANGRUN PHARMA
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