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A kind of preparation method of rho kinase inhibitor y27632 compound

A technology of Y27632 and kinase inhibitors, which is applied in the field of compound preparation, can solve the problems of expensive rhodium catalysts and impracticality, and achieve the effects of good reactions in each step, suitable for large-scale production, and easy acquisition

Active Publication Date: 2016-01-20
兰州耀诚医药科技有限公司
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Problems solved by technology

Although this method can well ensure the optical activity of amines, it needs hydrogenation under high temperature and high pressure conditions, and the rhodium catalyst is expensive, so this method is not very practical

Method used

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  • A kind of preparation method of rho kinase inhibitor y27632 compound
  • A kind of preparation method of rho kinase inhibitor y27632 compound
  • A kind of preparation method of rho kinase inhibitor y27632 compound

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preparation example Construction

[0024] like figure 1 As shown, the present invention discloses a preparation method of a Rho kinase inhibitor Y27632 compound, comprising the following steps:

[0025] a, raw material compound 1 namely (trans)-1,4-cyclohexanedicarboxylic acid monoester and dimethyl hydroxylamine are added to N 2 In a protected three-necked flask, dichloromethane and EDCI were subsequently added. Add N,N'-dimethylaminopyridine at 0°C and stir overnight at room temperature. The reaction solution was washed with water and extracted with dichloromethane, the organic phases were combined, and then successively washed with hydrochloric acid, saturated NaHCO 3 , water and saturated NaCl solution. The organic phase was dried and concentrated by filtration to obtain compound 2 (trans)-4-(N-methoxy-N-methylformamide)cyclohexylcarboxylate.

[0026] b. Add the compound 2 into a three-necked flask, and then add THF. in N 2 Under protection, the temperature was lowered to -20°C, kept for 10 minutes, a...

Embodiment 1

[0036] A preparation method of a Rho kinase inhibitor Y27632 compound, the method comprising the following steps:

[0037] a. Add raw material compound 1, trans-monomethyl cyclohexanedicarboxylate (100g, 537.03mmol) and dimethylhydroxylamine (63.05g, 644.43mmol) into a 2L three-necked flask protected by nitrogen, and then add dichloromethane (1500 mL) and EDCI (154.42 g, 805.54 mmol). The reaction flask was cooled to 0°C in an ice-water bath, and then N,N'-dimethylaminopyridine (65.52g, 537.03mmol) was added, the reaction system changed from colorless to yellow, and the temperature of the reaction system was raised to Stir overnight at room temperature. The reaction solution was mixed with 500mLH 2 O water was washed three times, and the aqueous phase was extracted twice with 200 mL of dichloromethane. The organic phases were combined, and then successively washed with 600mL of 0.5N hydrochloric acid, saturated NaHCO 3 , water and saturated NaCl solution twice each. The o...

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Abstract

The invention discloses a preparation method of a Rho kinase inhibitor Y27632 compound. Chirality of amine is constructed through a CBS reduction method high in selectivity to obtain amine with high optical purity, thus effectively and rapidly realizing synthesis of the Y27632 compound; moreover, the preparation method disclosed by the invention is simple, and raw materials and reagents required are low in cost and easy to acquire; and the preparation method is good in various reaction steps, high in selectivity, mild in condition during a synthesis process and applicable to mass production.

Description

technical field [0001] The invention relates to a preparation method of a compound, in particular to a preparation method of a Rho kinase inhibitor Y27632 compound. Background technique [0002] Compound Y27632 is a highly active and selective Rho kinase inhibitor, which plays an important role in understanding the physiological role of Rho kinase. As an important biochemical reagent, Y27632 is widely used in the research of Rho-associated protein kinase signaling channel. Y27632 is also widely used in the research of treatment and diagnosis of various diseases (such as cardiovascular disease, cancer, AIDS). Therefore, it is of great significance to synthesize and prepare Y27632 efficiently and practically. [0003] The chemical structural formula of Y27632 is as follows: [0004] [0005] In the prior art, for the synthesis of Y27632, two synthesis methods have been reported in the literature. One method is reported in WO2004 / 022541. This method uses 1,4-dimethylolcy...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/75
CPCC07D213/75
Inventor 阿不都赛米.马木提贲一飞
Owner 兰州耀诚医药科技有限公司
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