Preparation method of bilastine intermediate

A bilastine and intermediate technology, which is applied to the preparation field of bilastine intermediates, can solve problems such as complicated operations, and achieve the effects of simple post-processing, low cost and short steps.

Pending Publication Date: 2020-09-22
BEIJING VENTUREPHARM BIOTECH
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The original research patent uses p-toluenesulfonyl chloride in the process of preparing the intermediate. Although the reaction conditions are mild in this step, the operation is cumbersome

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of bilastine intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Embodiment 1: the synthesis of compound 2

[0022] 5.00 g (19.1 mmoL) of 4-[1-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)-1-methylethyl]phenethyl alcohol (compound 1) and di Add 50 mL of methyl chloride into a 250 mL single-necked bottle, start stirring, add 2.50 g (21.0 mmoL) of thionyl chloride dropwise, and stir for 45 minutes. Add 50 ml of water to wash, separate the layers, and concentrate the organic phase. Compound 2 was obtained, 4.02 g, yield 75.2%.

Embodiment 2

[0023] Embodiment 2: the synthesis of compound 2

[0024] 4-[1-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)-1-methylethyl]phenethyl alcohol (compound 1) 10.00 g (38.2mmoL) and chloroform Add 100mL into a 250mL single-necked bottle, start stirring, add 5.00 g (42.0mmoL) of thionyl chloride dropwise, and stir for 60 minutes. Add 100 ml of water to wash, separate the layers, and concentrate the organic phase. Compound 2 was obtained, 8.57g, yield 80.1%.

Embodiment 3

[0025] Embodiment 3: the synthesis of compound 3

[0026] Weigh 5.00g (17.9mmoL) of 2-{2-[4-(2-chloroethyl)phenyl]propyl}-4,5-dihydro-4,4-dimethyloxazole (compound 2) , 1-(2-ethoxy-ethyl)-2-piperidin-4-yl-1H-benzimidazole 5.37g (19.6mmoL), K 2 CO 3 Add 3.7 g and 50 mL of DMF into a 250 ml three-necked flask, heat to 90°C, and stir for 3 h. Cool down to room temperature, add 80 mL of water, filter with suction, collect the filter cake and put it in a blast oven for drying to obtain 7.70 g of the target compound 3 with a yield of 83.4%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention discloses a preparation method of a bilastine intermediate, and particularly relates to a preparation method of 2-[1-(2-{4-[1-(4,4-dimethyl-4,5-2H-oxazole-2-yl)-1-methyl-ethyl]phenyl}-ethyl)-piperidine-4-yl]-1-(2-ethoxy-ethyl)-1H-benzimidazole. The preparation method has the advantages of short steps, simple post-treatment and low cost, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of a novel bilastine intermediate. Background technique [0002] Bilastine, a second-generation histamine H1 receptor antagonist developed by FAES in Spain, was approved in the European Union in 2010. Bilastine is mainly used for the treatment of allergic rhinitis, urticaria and chronic asthma. The Chinese chemical name of bilastine is: 2-[4-(2-(4-(1-(2-ethoxyethyl)-benzimidazol-2-yl)piperidin-1-yl)ethyl Base) phenyl] -2-methyl propionic acid, its structural formula is as follows: [0003] [0004] The original research patent uses p-toluenesulfonyl chloride in the process of preparing the intermediate. Although the reaction conditions are mild in this step, the operation is cumbersome. Contents of the invention [0005] The invention provides a bilastine intermediate 2-[1-(2-{4-[1-(4,4-dimethyl-4,5-2H-oxazol-2-yl)-1 -Methyl-ethyl] phenyl}-ethyl)-piperidin-4-yl]-1-(2-ethoxy-ethyl)-1H-benzimidazole ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C07D413/14
CPCC07D413/14
Inventor 马国辰李恩民赵国磊
Owner BEIJING VENTUREPHARM BIOTECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap