Preparation method and application of iodo-pyrrolotriazine amine compound

A technology for amine compounds and iodopyrrole, which is applied to the preparation method and application field of iodopyrrolotriazine amine compounds, can solve the problems of separation and purification of target products, and the reaction is not green enough, and achieves mild reaction conditions, The effect of simple post-processing and easy availability of raw materials

Pending Publication Date: 2022-03-01
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existing iodination method is to prepare the target compound by reacting pyrrolo[2,1-F][1,2,4]triazine-4-amine with stoichiometric NIS (N-iodosuccinimide) , but after th

Method used

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  • Preparation method and application of iodo-pyrrolotriazine amine compound
  • Preparation method and application of iodo-pyrrolotriazine amine compound
  • Preparation method and application of iodo-pyrrolotriazine amine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] Preparation of 7-iodopyrrolo[2,1-F][1,2,4]triazin-4-amine

[0066] Add sodium iodide 0.5mmol (1.0equiv), diphenyl sulfoxide 1.5mmol (1.5equiv) and toluene (as solvent) in the reaction bottle, add hydrochloric acid (2.5equiv.) under stirring, then place the reaction bottle in the Stir in an oil bath at 30°C for 1.0h. Then add pyrrolo[2,1-F][1,2,4]triazin-4-amine 0.5mmol (1.0equiv, make the substrate concentration 0.05M) to it, then heat to 65°C, and detect the reaction until After the raw material is consumed, it is quenched after cooling to room temperature, extracted with ethyl acetate, dried, and the solvent is removed by distillation under reduced pressure to obtain the crude product 7-iodopyrrolo[2,1-F][1,2,4]triazine -4-amine, the calculated yield of the target product is 52%.

[0067] 1 H NMR (400MHz, DMSO-d 6 )δ7.91(s, 1H), 7.79(br s, 2H), 6.97(d, J=4.4Hz, 1H), 6.80(d, J=4.4Hz, 1H). 13 C NMR (101MHz, DMSO-d 6 )δ155.7, 149.2, 118.8, 118.2, 104.4, 71.9. MS m / ...

Embodiment 2

[0069] Preparation of 7-iodopyrrolo[2,1-F][1,2,4]triazin-4-amine

[0070] Same as Example 1, only change the reaction solvent, the reaction solvent is acetonitrile (making the substrate concentration 0.05M) the yield of the target product, 63%.

Embodiment 3

[0072] Preparation of 7-iodopyrrolo[2,1-F][1,2,4]triazin-4-amine

[0073] Same as Example 1, only change the reaction solvent, the reaction solvent is tetrahydrofuran (to make the substrate concentration 0.05M), the yield of the target product: 47%.

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Abstract

The invention discloses a preparation method and application of an iodo-pyrrolo-triazine amine compound, and the method at least comprises the following steps: adding a pyrrolo-[2, 1-F] [1, 2, 4] triazine-4-amine compound into a reaction system I containing an iodized salt, a sulfoxide compound and an acidic compound, and reacting to obtain the iodo-pyrrolo-triazine amine compound. The preparation method provided by the invention has the advantages of simple and easily available raw materials, no transition metal participation, mild reaction conditions, simple post-treatment, high yield and the like.

Description

technical field [0001] The application relates to a preparation method and application of iodopyrrolotriazine amine compounds, belonging to the field of organic synthesis. Background technique [0002] Organic iodides are widely used in the fields of drug preparation, natural product synthesis, and new material preparation. The preparation of organic iodides by directly forming C-I bonds from C-H bonds through green iodination methods is even more popular. [0003] At present, nucleoside drugs are an important class of drugs used clinically to treat viral infections, tumors, and AIDS. Nearly 50% of the antiviral drugs used are nucleoside drugs. Pyrrolotriazine amine compounds are often included in the backbone of nucleoside drugs, such as kinase inhibitors, remdesivir, protease inhibitors, etc., and play an important role in the development of related drugs. [0004] Iodopyrrolotriazine amines are compounds that are important synthetic fragments for the synthesis of pyrrolo...

Claims

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Application Information

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IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 李灿刘䶮雷文龙
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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