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a n 2 - Polyfluoroalkyl acyl guanidine compound and preparation method thereof

A technology of polyfluoroalkylacylguanidine and guanidine compounds, which is applied in the field of preparation of N2-polyfluoroalkylacylguanidine compounds, and achieves the effects of novel structure, cheap and easy-to-obtain raw materials, and specific stereoselectivity

Active Publication Date: 2021-05-28
LIAONING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Summarizing the existing methods for the synthesis of acylguanidine derivatives, it is not difficult to see that most methods require the use of toxic acyl halide reagents

Method used

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  • a n <sup>2</sup> - Polyfluoroalkyl acyl guanidine compound and preparation method thereof
  • a n <sup>2</sup> - Polyfluoroalkyl acyl guanidine compound and preparation method thereof
  • a n <sup>2</sup> - Polyfluoroalkyl acyl guanidine compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1 Nitrogen-(bis(dimethylamino)methylene)-2,2,3,3,4,4,4-heptafluorobutanamide

[0033] 1. At room temperature, tetramethylguanidine (1.0 mmol) was put into a 25 mL round bottom flask, and 2 mL of acetonitrile (water content 0.1%) solvent was injected. Then, perfluoroiodobutane (1.1 eq) was added. Under the irradiation of 36W CFL lamp, the reaction was monitored by TLC until the reaction was complete (about 10h). The resulting reaction product was poured into 100 mL of water, extracted three times with dichloromethane, the organic phases were combined, dried, and the organic solvent was distilled off under reduced pressure to obtain a crude product.

[0034] 2. the crude product is carried out to silica gel column chromatography (silica gel needs to use Et 3 N / PE=1:9 immersion overnight pretreatment), eluting with eluent (petroleum ether: ethyl acetate=1:1 (V:V)), collecting the eluate, and distilling under reduced pressure to obtain a white solid , which is th...

Embodiment 2

[0041] Example 2 (E)-nitrogen-(amino(dimethylamino)methylene)-2,2,3,3,4,4,4-heptafluorobutanamide

[0042] 1. At room temperature, put 1,1-dimethylguanidine hydrochloride (1.0mmol) and sodium hydroxide (1.0eq) into a 25mL round bottom flask, inject 2mL of acetonitrile (water content 0.1%) solvent, and neutralize for 4h The acid was removed, then perfluoroiodobutane (1.1 eq) was added. The reaction was performed under 36W CFL light irradiation, and monitored by TLC until the reaction was complete (about 12h). The resulting reaction product was poured into 100 mL of water, extracted three times with dichloromethane, the organic phases were combined, dried, and the organic solvent was distilled off under reduced pressure to obtain a crude product.

[0043] 2. the crude product is carried out to silica gel column chromatography (silica gel needs to use Et 3 N / PE=1:9 immersion overnight pretreatment), eluting with eluent (petroleum ether: ethyl acetate=1:1 (V:V)), collecting the ...

Embodiment 3

[0050] Example 3 Nitrogen-(diaminomethylene)-2,2,3,3,4,4,4-heptafluorobutanamide

[0051] 1. At room temperature, put guanidine hydrochloride (1.0mmol) and sodium hydroxide (1.0eq) into a 25mL round bottom flask, inject 2mL of acetonitrile (water content 0.1%) solvent, neutralize for 4h to remove acid, and then add all Fluoroiodobutane (1.1 eq). The reaction was performed under 36W CFL light irradiation, and monitored by TLC until the reaction was complete (about 14h). The resulting reaction product was poured into 100 mL of water, extracted three times with dichloromethane, the organic phases were combined, dried, and the organic solvent was distilled off under reduced pressure to obtain a crude product.

[0052] 2. the crude product is carried out to silica gel column chromatography (silica gel needs to use Et 3 N / PE=1:9 immersion overnight pretreatment), eluting with eluent (petroleum ether: ethyl acetate=1:1 (V:V)), collecting the eluate, and distilling under reduced pre...

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Abstract

The present invention relates to a kind of N 2 ‑Polyfluoroalkylacylguanidine compound and its preparation method. The N 2 ‑Polyfluoroalkylacylguanidine compounds have the structure of general formula (I) or (II). The synthesis method of this type of compound comprises the following steps: placing guanidine compounds or urea compounds or imidazoline compounds in a reaction flask, adding organic solvents and polyfluoroalkyl halides, stirring at room temperature and under light for 6-15 hours, The end point of the reaction is monitored by TLC; the resulting product is poured into water, extracted with dichloromethane, the organic phase is collected, dried, and the solvent is distilled off under reduced pressure; the obtained crude product is separated and purified by silica gel column chromatography to obtain N 2 ‑Polyfluoroalkylacylguanidine products. The synthesis route of the present invention has the advantages of simple method, low cost, wide range, mild conditions, safe reaction route, easy operation and the like. Such compounds can be used as potential histamine H 2 use of receptor agonists. or

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a kind of N 2 -A method for the preparation of polyfluoroalkylacylguanidine compounds. Background technique [0002] Guanidino is a common structural unit that exists widely in many drugs and natural products. Moreover, guanidino-Lewis bases can also be used as catalysts in many organic chemical reactions. N involved in the present invention 2 Due to its unique structural characteristics, -polyfluoroalkylacylguanidine will attract more people to explore its theory and practical application. So far to N 2 -There are few reports on the synthesis of such compounds as polyfluoroalkyl acyl guanidine, and some of the main synthetic methods of acyl guanidine derivatives reported in the literature include: 1) using a dehydrating agent, 2-chloro-1,3-dimethyl Imidazolium salt, under the condition that triethylamine is made base, and methylene chloride is solvent, nucleophili...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C279/22C07C277/08C07D295/215C07D231/12C07D233/48
CPCC07C277/08C07C279/22C07D231/12C07D233/48C07D295/215
Inventor 梁福顺汪锐苏忠民
Owner LIAONING UNIVERSITY
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