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

A technology of aminopyrrole and amino, which is applied in the field of preparation of 4-amino-7-iodopyrrolo[2,1-f][1,2,4]triazine, can solve the problem of low product purity, difficult removal, di Problems such as high content of iodide impurities and isomer impurities, etc., to achieve the effect of high product yield, easy availability of raw materials, and high purity

Pending Publication Date: 2020-07-17
GUANGZHOU BIO CURRENT BIOLOGICAL TECH LTD
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  • Application Information

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Problems solved by technology

The reported method for the synthesis of 4-amino-7-iodopyrrolo[2,1-f][1,2,4]triazine is as follows: WO 2016069826 discloses the synthesis of 4-amino-7-iodosuccinimide and 4-amino The reaction of pyrrolo[2,1-f][1,2,4]triazine to prepare 4-amino-7-iodopyrrolo[2,1-f][1,2,4]triazine, obtained The purity of the product is low, the content of diiodide impurities and isomer impurities is relatively large, it is not easy to remove, and the yield is only about 50%

Method used

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

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Embodiment 1

[0038] A preparation method of 4-amino-7-iodopyrrolo[2,1-f][1,2,4]triazine, comprising the following steps:

[0039] 1) Under nitrogen protection, add 80g (0.6mol) of 4-aminopyrrolo[2,1-f][1,2,4]triazine into 400mL of N,N-dimethylformamide and stir well , lower the temperature to -25°C, add 181.8g (0.716mol, 1.2equiv) of iodine in equal amounts in batches, and react at -10°C for 3h after feeding is complete;

[0040] 2) Add 80 mL (1.35 mol) of acetic acid and 60 g (0.24 mol, 0.4 equiv) of N-iodosuccinimide in batches to the reaction solution in step 1), and react at -10°C for 1 h;

[0041] 3) Mix and stir 225.7g (1.791mol, 3equiv) of sodium sulfite, 101.2g (0.955mol, 1.6equiv) of sodium carbonate and 2000mL of water evenly, cool down to 5°C to obtain an alkali solution, and slowly add the alkali solution dropwise Into the reaction solution of step 2), adjust the pH of the system to 9 with saturated sodium carbonate solution after adding, stir for 2 hours, filter, the filtered...

Embodiment 2

[0043] A preparation method of 4-amino-7-iodopyrrolo[2,1-f][1,2,4]triazine, comprising the following steps:

[0044] 1) Under nitrogen protection, add 900g (6.71mol) of 4-aminopyrrolo[2,1-f][1,2,4]triazine into 4000mL of N,N-dimethylformamide and stir well , lower the temperature to -25°C, add 2000g (8.05mol, 1.2equiv) of iodine in equal amounts in batches, and react at -10°C for 3h after feeding is complete;

[0045] 2) Add 900 mL (15.74 mol) of acetic acid and 700 g (3.11 mol) of N-iodosuccinimide in batches to the reaction solution in step 1), and react at -10°C for 1 h;

[0046] 3) Mix and stir 2000g (15.87mol) of sodium sulfite, 1100g (10.38mol) of sodium carbonate and 20L of water evenly, cool down to 5°C to obtain an alkali solution, and slowly add the alkali solution dropwise to the reaction solution in step 2) After the addition, adjust the pH of the system to 9 with saturated sodium carbonate solution, stir for 2 hours, filter, and the filtered solid is beaten with ...

Embodiment 3

[0048] A preparation method of 4-amino-7-iodopyrrolo[2,1-f][1,2,4]triazine, comprising the following steps:

[0049] 1) Under nitrogen protection, add 80g (0.6mol) of 4-aminopyrrolo[2,1-f][1,2,4]triazine into 400mL of N,N-dimethylformamide and stir well , lower the temperature to -25°C, add 181.8g (0.716mol, 1.2equiv) of iodine in equal amounts in batches, and react at -10°C for 3h after feeding is complete;

[0050] 2) Add 80 mL (1.35 mol) of formic acid and 60 g (0.24 mol, 0.4 equiv) of N-iodosuccinimide in batches to the reaction solution in step 1), and react at -10°C for 1 h;

[0051] 3) Mix and stir 225.7g (1.791mol, 3equiv) of sodium sulfite, 101.2g (0.955mol, 1.6equiv) of sodium carbonate and 2000mL of water evenly, cool down to 5°C to obtain an alkali solution, and slowly add the alkali solution dropwise Into the reaction solution of step 2), adjust the pH of the system to 9 with saturated sodium carbonate solution after adding, stir for 2 hours, filter, the filtered...

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Abstract

The invention discloses a preparation method of 4-amino-7-iodopyrrolo [2, 1-f] [1, 2, 4] triazine. The preparation method comprises the following steps: reacting 4-aminopyrrolo [2, 1-f] [1, 2, 4] triazine with iodine or iodine chloride, and reacting with N-iodosuccinimide to obtain 4-amino-7-iodopyrrolo [2, 1-f] [1, 2, 4] triazine. The preparation method of 4-amino-7-iodopyrrolo [2, 1-f] [1, 2, 4]triazine has the advantages of easily available raw materials, simple process, mild reaction conditions, environmental protection, economy and the like, and is high in product yield, high in purity and suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of 4-amino-7-iodopyrrolo[2,1-f][1,2,4]triazine. Background technique [0002] Remdesivir is a nucleoside analog with antiviral activity against EBOV (EC 50 =70~140nM) and other filoviruses (EC 50 =0.019~1.48 μM) various variants showed antiviral activity. Remdesivir can inhibit EBOV replication, protect 100% of animals infected with EBOV from fatal diseases, improve clinical disease signs and pathophysiological indicators, and can also be used to treat Ebola virus infection with very good efficacy. Studies have found that remdesivir is not only effective against filoviruses such as Ebola virus, but also has inhibitory effects on respiratory syncytial virus, coronavirus, Nipah Virus, Hendra Virus, etc. Effect. In addition, it has been confirmed by in vitro cell experiments and animal model experiments that Remdesivir can have antiviral effects on both SARS-CoV and Middle East Respiratory Syndrome Coronav...

Claims

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Application Information

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IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 王勇李智敏尹灿强李雪辉
Owner GUANGZHOU BIO CURRENT BIOLOGICAL TECH LTD
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