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Preparation method of 4-amino-7-iodo pyrrolo [2, 1-f] [1, 2, 4] triazine

A technology of aminopyrrole and l-f, which is applied in the direction of organic chemistry, can solve the problems of high consumption of iodine-containing substances, low yield, and many impurities, and achieve the effects of high utilization rate, less by-products, and high reaction yield

Active Publication Date: 2021-01-08
威海同丰海洋生物科技有限公司
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Problems solved by technology

The method is prepared by the reaction of N-iodosuccinimide and 4-aminopyrrolo[2,1-f][1,2,4]triazine in the solvent N,N-dimethylformamide to prepare 4 -Amino-7-iodopyrrolo[2,1-f][1,2,4]triazine, but the yield of the reaction product is not high and there are more impurities
Although a new report (CN 111423443 A) has recently improved the above-mentioned method, that is, in the solvent N,N-dimethylformamide, 4-aminopyrrolo[2,1-f][1,2,4] Triazine reacts with iodine or iodine chloride first, and then reacts with N-iodosuccinimide to obtain 4-amino-7-iodopyrrolo[2,1-f][1,2,4]triazine, This method consumes more iodine-containing substances and has higher cost

Method used

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  • Preparation method of 4-amino-7-iodo pyrrolo [2, 1-f] [1, 2, 4] triazine
  • Preparation method of 4-amino-7-iodo pyrrolo [2, 1-f] [1, 2, 4] triazine
  • Preparation method of 4-amino-7-iodo pyrrolo [2, 1-f] [1, 2, 4] triazine

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preparation example Construction

[0037] Based on this, the present invention provides a kind of preparation method of 4-amino-7-iodopyrrolo[2,1-f][1,2,4]triazine, can be divided into following two methods:

[0038] The first method: 4-aminopyrrolo[2,1-f][1,2,4]triazine reacts with hydroiodide and an oxidizing agent to obtain 4-amino-7-iodopyrrolo[2,1 -f][1,2,4]triazine, the reaction formula is as follows:

[0039]

[0040] The second method: 4-aminopyrrolo[2,1-f][1,2,4]triazine reacts with iodine molecules first, and then reacts with an oxidant to obtain 4-amino-7-iodopyrrolo[2, 1-f][1,2,4]triazine, the reaction formula is as follows:

[0041]

[0042] Principle of the present invention is as follows:

[0043]In the first method, an inexpensive oxidizing agent is used to react with hydroiodide to generate reactive molecular iodine, which is then reacted with 4-aminopyrrolo[2,1-f][1,2,4]triazine to obtain the product; in In the second method, molecular iodine is first reacted with 4-aminopyrrolo[2,1-f...

Embodiment 1

[0046] Under nitrogen protection, 3.5g (26.1mmol) of 4-aminopyrrolo[2,1-f][1,2,4]triazine and 4.3g (26.1mmol, 1.0equiv) of potassium iodide were added to 15mL of Methanol, stir well. Cool down to 0°C, add 16.0g (26.1mmol, 1.0equiv) potassium hydrogen persulfate compound salt (Oxone) in equal amounts in batches, and react while feeding for a total of 3 hours. 100 mL of water and 6.5 g of sodium thiosulfate were added, and then the pH value of the reaction solution was adjusted to alkaline with saturated sodium bicarbonate solution. The reaction solution was extracted with ethyl acetate, the organic phase was washed, dried, filtered and desolvated under reduced pressure to obtain 6.0 g of 4-amino-7-iodopyrrolo[2,1-f][1,2,4]triazine (purity greater than 98%, yield 88%).

[0047] That 1 H NMR data are as follows: 1 H-NMR (400MHz, DMSO-d 6 ): 7.91 (s, 1H), 7.90-7.70 (br, 2H), 7.00 (d, J=3.5Hz, 1H), 6.84 (d, J=3.6Hz, 1H).

Embodiment 2

[0049] Under nitrogen protection, 35g (0.261mol) of 4-aminopyrrolo[2,1-f][1,2,4]triazine and 86g (0.522mol, 2.0equiv) of potassium iodide were added to 150mL of methanol , stir well. Cool down to 0°C, add 160g (0.261mol, 1.0equiv) potassium hydrogen persulfate compound salt (Oxone) in equal amounts in batches, and continue the reaction for another 7 hours to complete the reaction. Add 1000 mL of water and 65 g of sodium thiosulfate, and then adjust the pH of the reaction solution to alkaline with saturated sodium bicarbonate solution. Stir, filter, the filtered solid is beaten with water and ethanol, filtered, and vacuum-dried to obtain 61.1g of 4-amino-7-iodopyrrolo[2,1-f][1,2,4]triazine (purity greater than 96 %, yield 90%).

[0050] That 1 H NMR data are as follows: 1 H-NMR (400MHz, DMSO-d 6 ): 7.91 (s, 1H), 7.90-7.70 (br, 2H), 7.00 (d, J=3.5Hz, 1H), 6.84 (d, J=3.6Hz, 1H).

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Abstract

The invention discloses a preparation method of 4-amino-7-iodo pyrrolo [2, 1-f] [1, 2, 4] triazine, which comprises the following steps: reacting 4-amino pyrrolo [2, 1-f] [1, 2, 4] triazine with an iodine-containing substance and an oxidant to obtain 4-amino-7-iodo pyrrolo [2, 1-f] [1, 2, 4] triazine; wherein the iodine-containing substance is iodine or a hydroiodate; the oxidantis at least one ofpotassium hydrogen persulfate composite salt, hydrogen peroxide, m-chloroperoxybenzoic acid, tert-butyl hydroperoxide, sodium hypochlorite, ammonium persulfate and sodium persulfate. According to thepreparation method disclosed by the invention, the preparation is simpler, and the 4-amino-7-iodo pyrrolo [2, 1-f] [1, 2, 4] triazine can be obtained in one step; the preparation method has the characteristics of readily available and cheap raw materials, simple process, mild reaction conditions, high product yield, high iodine atom utilization rate and the like.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis of drugs, in particular to a new method for preparing 4-amino-7-iodopyrrolo[2,1-f][1,2,4]triazine. Background technique [0002] Remdesivir is a nucleoside compound developed by Gilead in the United States and is a broad-spectrum antiviral drug. Previous studies have confirmed that remdesivir has certain effectiveness against severe acute respiratory syndrome (SARS) and Middle East respiratory syndrome (MERS), and the drug has also been used in clinical trials against Ebola virus infection. Since the new crown pneumonia virus has a similar structure to coronaviruses such as SARS and MERS, it can be speculated that Redcivir may also be effective in targeting the new crown pneumonia virus. In vitro experiments have shown that remdesivir has a good inhibitory effect on the new coronary pneumonia virus. [0003] Remdesivir is a synthetic drug, and the synthetic route has been reported. Th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 严捷吴学记
Owner 威海同丰海洋生物科技有限公司
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