Synthesis process of ribavirin intermediate and the intermediate

A technology of ribavirin and synthesis process, which is applied in the field of synthesis of ribavirin intermediates, can solve the problems of complicated synthesis technical route, difficult operation and high danger, and achieves simple and easy-to-obtain raw materials, simple operation and low production cost Effect

Active Publication Date: 2020-07-31
广安润康药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0019] The object of the present invention is to provide a synthesis process of ribavirin intermediates, the synthesis process raw material cost is low and safe, the reaction conditions are mild, the synthesis route is short and pollution-free, to solve the existing technical route of ribavirin intermediate synthesis Problems of cumbersome, difficult operation, high risk, high cost and pollution

Method used

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  • Synthesis process of ribavirin intermediate and the intermediate
  • Synthesis process of ribavirin intermediate and the intermediate
  • Synthesis process of ribavirin intermediate and the intermediate

Examples

Experimental program
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Effect test

Embodiment 1

[0075] A kind of synthetic technique of ribavirin intermediate 1,2,4-triazole-3-carboxamide, synthetic route (in structural formula A, B, C, R 1 =R 2 =-CH 3 ):

[0076]

[0077] Synthetic operation steps:

[0078] S1: 500mL three-necked bottle, equipped with magnetic stirring and thermometer; add 200mL of anhydrous methanol into it, add monohydrazide methyl oxalate (compound A) (59g, 0.5mol) into it under stirring, and then add trimethyl orthoformate in one go Ester (106.1g, 1.0mol), react at room temperature for 4h; after the reaction, concentrate and recover methanol and excess trimethyl orthoformate; the residue is oxalic acid monohydrazide methyl ether (oxalhydrazide methyl ether compound B, R 1 =R 2 =Me) 76g, theoretical yield: 95%. 1 H NMR (400MHz, DMSO-d 6 ) shows that the crude product is a mixture of four geometric isomers, which is consistent with the structure of two pairs of double bonds in the molecule. in, 1 HNMR (DMSO-d 6 ) spectrum (such as figure ...

Embodiment 5

[0081] According to the method of "Example 5", the product 1,2,4-triazole-3-carboxamide obtained in this step can be converted into 1,2,4-triazole-3-carboxylic acid methyl ester, proving that 1, The chemical structure of 2,4-triazole-3-carboxamide is correct.

Embodiment 2

[0083] This embodiment is based on embodiment 1, and the difference with embodiment 1 is:

[0084] What step S1 synthesized is oxalic acid monohydrazide ethyl ether B (R 1 =R 2 =Et), step S2 is starting raw material with oxalic acid monohydrazide ethyl ether, and the synthetic process of oxalic acid monohydrazide ethyl ether is as follows:

[0085] 500mL three-necked bottle equipped with magnetic stirring and thermometer, add 200mL of absolute ethanol, then add ethyl oxalic acid monohydrazide (0.5mol, R 1 =CH 3 CH 2 -), triethyl orthoformate (0.5mol), heated to reflux for 2h; after the reaction, concentrated. The residue is oxalic acid monohydrazide ethyl ether B (R 1 =R 2 =Et), yield 95%.

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Abstract

The invention discloses a synthesis process of a ribavirin intermediate and the intermediate. 2-hydrazinyl-2-oxoacetate is used as a raw material, and the ribavirin intermediate 1,2,4-triazole-3-formamide is obtained by condensation with orthoformate triester, ammonolysis and cyclization in sequence. According to the process, the 2-hydrazinyl-2-oxoacetate is adopted as the initial raw material, the raw material is easily available and cheap, the synthesis route is short, expensive raw materials such as hypophosphorous acid are not adopted, dangerous raw materials such as hydrogen peroxide arenot used, a diazotization reaction which is a dangerous process is not adopted, reaction condition is mild, the whole process is almost free of generation of wastewater and solid waste; and the process is green, simple to operate and high in yield.

Description

technical field [0001] The invention relates to the technical field of synthesis of ribavirin intermediates, in particular to a synthesis process and intermediates of ribavirin intermediates. Background technique [0002] With the development of economic globalization, global warming and the massive abuse of antibiotics by humans, many bacteria have strong drug resistance, and their genes mutate rapidly, such as "SARS", "bird flu", " Viruses such as type A "HlNl" and "2019-nCoV" (new coronavirus pneumonia) have seriously endangered human health, leading to a sharp increase in the amount of antiviral drugs. Ribavirin is one of the very important antiviral drugs. Ribavirin (English: Ribavirin), also known as ribavirin, ribavirin, Niscor, etc., was synthesized by ICN pharmaceutical company Joseph T. Witkowski in 1970. It is a broad-spectrum and potent antiviral drug, which is a synthetic nucleoside drug and has inhibitory effects on many DNA and RNA viruses. It is used by the...

Claims

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Application Information

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IPC IPC(8): C07D249/10C07C257/22C07C257/20
CPCC07C257/20C07C257/22C07D249/10
Inventor 谈平忠谈平安魏巍黄明辉田晨煦
Owner 广安润康药业有限公司
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