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1,2,3-thiadiazole-5-formamidine compound containing three N-heterocycles and synthesis

A compound, thiadiazole technology, applied in the field of 1,2,3-thiadiazole compounds and their synthesis, can solve the problems of many by-products, low reactivity, low yield, etc., and achieve good economic benefits and social benefits benefit effect

Inactive Publication Date: 2015-05-13
XIHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Although there are many methods for synthesizing amidines at present, these methods are highly reactive for the synthesis of N-trisubstituted-1,2,3-thiadiazole-5-carboxamidine compounds with three aromatic rings reported by the present invention. Low, many by-products, low yield

Method used

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  • 1,2,3-thiadiazole-5-formamidine compound containing three N-heterocycles and synthesis
  • 1,2,3-thiadiazole-5-formamidine compound containing three N-heterocycles and synthesis
  • 1,2,3-thiadiazole-5-formamidine compound containing three N-heterocycles and synthesis

Examples

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Effect test

Embodiment 1

[0030] Example 1: Synthesis of N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-N'-(pyridin-4-yl)-N,4-dimethyl-1, 2,3-Thiadiazole-5-carboxamidine (TDCA-1)

[0031] 1) Preparation of catalyst trimethylsilyl polyphosphate:

[0032]Under the condition of nitrogen protection, add 50ml of the dried solvent dichloromethane, phosphorus pentoxide (14.2g, 50mmol) and hexamethyldisiloxane (25.6g, 160mmol) successively into the dry three-neck reaction flask, and heat to reflux After reacting for 1 hour, the reflux reaction device was changed to a distillation reaction device, and the temperature was gradually raised to 160 ° C. During the heating process, the low boiling point solvent and unreacted hexamethyldisiloxane were distilled off, and kept at 160 ° C for 1 hour. 27.8 g of the obtained syrupy liquid (the liquid is trimethylsilyl polyphosphate), was isolated from the air, and was directly used in the next step reaction (preparation of TDCA-1) without further treatment.

[0033]

[0034]...

Embodiment 2

[0036] Example 2: Synthesis of N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-N'-(2,6-difluoropyridin-4-yl)-N,4- Dimethyl-1,2,3-thiadiazole-5-carboxamidine (TDCA-10):

[0037] 1) Preparation of the catalyst trimethylsilyl polyphosphate: The catalyst trimethylsilyl polyphosphate was prepared according to the same method as in Example 1.

[0038]

[0039] 2) Preparation of TDCA-10

[0040] Under the condition of nitrogen protection, 600ml of anhydrous sulfolane, 2,6-difluoro-4-aminopyridine (26.2g, 200mmol), compound B (N-(5-tert-butyl-1, 3,4-thiadiazol-2-yl)-N,4-dimethyl-1,2,3-thiadiazole-5-carboxamide) (59.6g, 200mmol), adding freshly distilled thionyl chloride (59.5g, 500mmol), after heating to reflux for 2 hours, the reaction was changed from a reflux device to a distillation device, and the low-boiling components in the reactor were distilled (the main component was unreacted thionyl chloride), and phosphorus pentoxide was added Solid (14.2g, 50mmol), add 27.8g of the above-m...

Embodiment 3

[0042] Synthesis of N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-N'-(2,6-difluoropyridin-4-yl)-N,4-dimethyl- 1,2,3-Thiadiazole-5-carboxamidine (TDCA-10):

[0043] According to the same method as in Example 2, the solid dosage of phosphorus pentoxide is 0g, and the other dosage and post-treatment process are unchanged to obtain the target compound N-(5-tert-butyl-1,3,4-thiadiazol-2-yl )-N'-(2,6-difluoropyridin-4-yl)-N,4-dimethyl-1,2,3-thiadiazole-5-carboxamidine ( TDCA-10 ), white solid 37.5g, liquid phase normalized content 97.9%, yield 45.9%.

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Abstract

The invention discloses an N-trisubstituted-1,2,3-thiadiazole-5-formamidine compound with three aromatic rings of general formula TDCA and a synthesis method of N-trisubstituted-1,2,3-thiadiazole-5-formamidine compound. The target compound of general formula TDCA is obtained by reacting a compound of general formula B and a compound of general formula A, wherein references of X and Y in the general formula A are the same as those in the general formula TDCA.

Description

technical field [0001] The present invention relates to 1,2,3-thiadiazole compounds and their synthesis methods, especially N-trisubstituted-1,2,3-thiadiazole-5-carboxamidine compounds with novel chemical structure and their synthesis methods . Background technique [0002] Amidines have a wide range of applications in medicine, and can be used as drugs for treating diabetes, cardiovascular diseases, anti-inflammatory drugs, anthelmintics and diuretics. For example, the cyclic amidine compound described in Formula 1 has a vasodilator effect and is used for the treatment of hypertension. The aryl-substituted amidine compound containing multiple iodines described in Formula 2 has higher selectivity to tuberculosis fungus, and its cholepicamidine sodium is an oral cholecystectomy and cholangiography drug. Low toxicity, few side effects, safe for patients. Compared with traditional medicines, the angiography is quick, the patient does not need to fast, and the imaging effect ...

Claims

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Application Information

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IPC IPC(8): C07D417/14
CPCC07D417/14
Inventor 王会镇刘萍杨维清张燕任川洪
Owner XIHUA UNIV
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