Ionic liquid and method for synthesizing Thiazovivin by same

An ionic liquid and compound technology, applied in the direction of organic chemistry, can solve the problems of complex operation, high cost, difficult monitoring, etc., and achieve the effect of simple operation, low cost and high yield

Active Publication Date: 2017-05-10
LANZHOU INST OF ANIMAL SCI & VETERINARY PHARMA OF CAAS +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Aiming at the problems in the art that the existing synthesis method of Thiazovivin as mentioned above is complex in operation, difficult in monitoring and too high in cost, the present invention provides a method for synthesizing Thiazovivin by using ionic liquid branching technology

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  • Ionic liquid and method for synthesizing Thiazovivin by same
  • Ionic liquid and method for synthesizing Thiazovivin by same
  • Ionic liquid and method for synthesizing Thiazovivin by same

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Embodiment 1

[0073] Embodiment 1, ionic liquid of the present invention and preparation method thereof

[0074] The present embodiment provides a kind of ionic liquid for synthesizing Thiazovivin, it is characterized in that, described ionic liquid has the structure shown in following general formula 1:

[0075]

[0076] where R is selected from

[0077] x is selected from Cl, Br, I, BF 4 、PF 6 , ClO 4 、H 2 PO 4 , TS, ClO 4 , Lac, OAc, DCA, HSO 4 , NO 3 、HSO 4 , TFMS, NTF 2 , TSA, FSI;

[0078] n is any natural number in 0-10.

[0079] In the above general formula, the carbon chain can be shortened or lengthened, and the benzene ring part It is necessary, because this structure can selectively remove the ionic liquid by TFA when removing the ionic liquid, without affecting another benzyl group connected to the N atom; theoretically, This part of the structure can be in any form, the imidazole-type ionic liquid provided in the preferred embodiment of the present inventio...

Embodiment 2

[0088] Embodiment 2, the method for synthesizing Thiazovivin according to the present invention

[0089] The present embodiment provides a method for synthesizing Thiazovivin, comprising the following steps:

[0090] (1) prepare ionic liquid;

[0091] (2) connecting the ionic liquid with benzylamine to obtain compound 4;

[0092]

[0093] (3) Acylation reaction of the above compound 4 with 2-bromothiazole-4-carboxylic acid to obtain compound 5;

[0094]

[0095] (4) Amination of the above compound 5 with 4-aminopyrimidine to obtain compound 6;

[0096]

[0097] (5) The Thiazovivin can be obtained by removing the ionic liquid in the above compound 6;

Embodiment 3

[0098] Embodiment 3, using the method of the present invention to synthesize Thiazovivin (1)

[0099] Based on the ionic liquid provided in Example 2, this embodiment provides specific steps for synthesizing Thiazovivin by the method of the present invention, such as figure 2 shown, including the following steps:

[0100] Under nitrogen protection, using the ionic liquid (4.50 g, 10.0 mmol) provided in Example 2, benzylamine (2.2 ml, 20.0 mmol), sodium cyanoborohydride (NaCNBH 3 , 2.48 g, 40.0 mmol) was dissolved in dry methanol (100 mL). The reaction solution was stirred at room temperature for 12 hours. Thin layer chromatography showed that the reaction was complete. The solvent was evaporated to dryness under reduced pressure, then dissolved in dichloromethane (200 ml), and washed with 1M HCl, saturated NaHCO 3 and saturated NaCl extraction, organic phase with anhydrous NaCl 2 SO 4 After drying, filtering, and evaporating the solvent, the resulting mixture was purified...

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Abstract

The invention provides ionic liquid for synthesizing Thiazovivin, and belongs to the technical field of organic synthesis. The ionic liquid is of a structure as shown in the general formula 1. The invention further provides a Thiazovivin synthesizing method based on the ionic liquid. The Thiazovivin synthesizing method includes (1), connecting the ionic liquid to benzylamine to obtain a compound 4; (2), subjecting the compound 4 and 2-bromine thiazole-4-carboxylic acid to acylation reaction to obtain a compound 5; (3), subjecting the compound 5 and 4-aminopyrimidine to amination reaction to obtain a compound 6; (4), removing the ionic liquid in the compound 6 to obtain the Thiazovivin.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to an ionic liquid and a method for synthesizing Thiazovivin by using it. Background technique [0002] Thiazovivin(1) is a novel ROCK inhibitor, which can significantly enhance the survival of human embryonic stem cells (hESCs) by more than 30 times after enzymatic hydrolysis, and its IC in a cell-free assay 50 0.5 μM. In addition, Thiazovivin can also effectively inhibit the endocytosis of E-cadherin, thereby stabilizing E-cadherin on the cell surface and restoring cell-cell interactions to protect hESCs in suspension lacking extracellular matrix (ECM) to avoid death in the liquid. The structural formula of Thiazovivin (1) is as figure 1 shown. [0003] Currently reported synthesis methods for Thiazovivin include solid-phase synthesis (WO2010065721) and chemical synthesis (Synthetic Communications 1, 43:2876-2882, 2013). The reaction in the solid-phase s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/60C07D417/12
CPCC07D233/60C07D417/12
Inventor 吴培星宋楠李纯玲韩涛刘中奇刘春晖陈翠翠
Owner LANZHOU INST OF ANIMAL SCI & VETERINARY PHARMA OF CAAS
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