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Synthesis method of 5-trifluoromethyl isoquinoline-8-formic acid

A technology of trifluoromethylisoquinoline and trifluoromethyl, which is applied in the field of synthesis of pharmaceutical intermediates, can solve problems such as the lack of synthesis steps, and achieve the effects of convenient operation and post-processing, simple raw materials, and simple synthetic routes

Active Publication Date: 2020-12-15
SUZHOU KANGRUN PHARMA
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Problems solved by technology

[0003] There is no synthetic route about 5-trifluoromethylisoquinoline-8-formic acid at present stage, only the synthetic route of synthetic 5-trifluoromethylisoquinoline, and its method is 2-trifluoromethyl cinnamic acid and Azidodiphenylphosphonate generates 1-chloro-5-trifluoromethylisoquinoline through a ring-closing reaction, but lacks subsequent synthetic steps, so subsequent synthetic methods need to be extended

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  • Synthesis method of 5-trifluoromethyl isoquinoline-8-formic acid

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[0041]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.

[0042] In the present invention, the synthesis process of 5-trifluoromethylisoquinoline-8-carboxylic acid is based on 4-trifluoromethylphenethylamine raw material and TFAA through amino protection, ring closure, hydrolysis, bromination, debromination of alkenes, Dehydroaromatization to obtain 5-trifluoromethylisoquinoline, and NBS for 8-bromination to obtain 8-bromo-5-trifluoromethylisoquinoline, and 5-trifluoromethyl through carbonyl insertion and hy...

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Abstract

The invention discloses a synthesis method of 5-trifluoromethyl isoquinoline-8-formic acid. The method comprises the steps of by using 4-trifluoromethyl phenylethylamine as a raw material, carrying out amino protection, cyclization, hydrolysis, bromination, debromination and alkene insertion and dehydroaromatization on the 4-trifluoromethyl phenylethylamine and TFAA to obtain 5-trifluoromethyl isoquinoline, and carrying out 8-bit bromination on the 5-trifluoromethyl isoquinoline and NBS to obtain 8-bromine-5-trifluoromethyl isoquinoline; and carrying out carbonyl insertion and hydrolysis to obtain the 5-trifluoromethyl isoquinoline-8-formic acid. The method is simple in synthetic route, reasonable in process selection, low in raw material cost, simple and easily available in raw materials,convenient to operate and post-treat, high in total yield, free of highly toxic reagents, easy to amplify and suitable for large-scale 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 5-trifluoromethylisoquinoline-8-carboxylic acid. Background technique [0002] 5-Trifluoromethylisoquinoline-8-carboxylic acid is a pharmaceutical intermediate of Guan Yu. The carboxyl group at the 8-position is a good modification group and is widely used in the design of prodrugs. The fat solubility of the original drug is enhanced by making an esterified prodrug, the oral absorption effect is improved, and the blood drug concentration is increased. And trifluoromethyl, as a kind of fluorine-containing substituent group, also has many excellent properties in improving the pharmacodynamic structure. Therefore, 5-trifluoromethylisoquinoline-8-carboxylic acid is often used as a modification group to improve the activity of drug candidate molecules. Among them, Garcia Collazo et al. developed a heteroarylaminoiso...

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Application Information

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IPC IPC(8): C07D217/02
CPCC07D217/02
Inventor 晋浩文徐卫良徐炜政
Owner SUZHOU KANGRUN PHARMA
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