Unlock instant, AI-driven research and patent intelligence for your innovation.

A kind of preparation cinacalcet hydrochloride intermediate and method

A technology for cinacalcet hydrochloride and an intermediate, which is applied in the field of medicine, can solve problems such as unfavorable production, and achieves the effects of simple method, easy availability of raw materials, and easy industrialization

Active Publication Date: 2022-02-01
廖艺
View PDF6 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0023] This method uses red aluminum as the reducing agent. Although red aluminum is more economical and stable, it needs to be made into a solution for the convenience of storage and transportation. In industrial production, iron needs to be transported through special pipelines, which is not conducive to mass production. production to achieve industrialization

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
  • A kind of preparation cinacalcet hydrochloride intermediate and method
  • A kind of preparation cinacalcet hydrochloride intermediate and method
  • A kind of preparation cinacalcet hydrochloride intermediate and method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Example 1 Preparation of (R)-3-bromo-N-(1-(naphthalene-1-yl)ethyl)propan-1-amine

[0062] Add 3-bromopropionaldehyde (13.6g, 0.1mol), (R)-1-naphthylethylamine (17.1g, 0.1mol) into anhydrous methanol (100mL), stir in ice-water bath for 2h, add cyano group three times Sodium borohydride (0.5mol), the molar ratio of the dosage for three times is 2:2:1, continue to stir for 2h, dropwise add 2mol / L hydrochloric acid (20mL) to quench the reaction, concentrate under reduced pressure, add 100mL of water to dilute, and Extract with ethyl acetate, separate the organic layer, add anhydrous sodium sulfate to dry, filter with suction, and concentrate under reduced pressure to obtain (R)-3-bromo-N-(1-(naphthalene-1-yl)ethyl)propan-1 - Amine (23.26 g, 0.08 mol), yield 79.65%. 1 HNMR (400MHz, CDCl 3 )8.02-7.95(m,2H),7.84-7.79(m,1H),7.54-7.45(m,3H),7.15(d,J=7.2Hz,1H),4.01(m,1H),3.62(t , J=7.6Hz, 2H), 2.78(m, 2H), 1.89(m, 2H), 1.32(d, J=7.6Hz, 3H). m / z: 292.07.

Embodiment 2

[0063] Example 2 Preparation of (R)-3-bromo-N-(1-(naphthalene-1-yl)ethyl)propan-1-amine

[0064] Add 3-bromopropionaldehyde (13.6g, 0.1mol), (R)-1-naphthylethylamine (17.1g, 0.1mol) into anhydrous methanol (100mL), stir in an ice-water bath for 2h, and add the cyano group at one time Sodium borohydride (0.5mol), continue to stir for 2h, dropwise add 2mol / L hydrochloric acid (20mL) to quench the reaction, concentrate under reduced pressure, add 100mL water to dilute, extract with ethyl acetate, separate the organic layer, add anhydrous sulfuric acid Sodium drying, suction filtration, and concentration under reduced pressure gave (R)-3-bromo-N-(1-(naphthalene-1-yl)ethyl)propan-1-amine (14.6g, 0.05mol) with a yield of 50 %.

Embodiment 3

[0065] Example 3 Preparation of (R)-3-bromo-N-(1-(naphthalene-1-yl)ethyl)propan-1-amine

[0066] Add 3-bromopropionaldehyde (13.6g, 0.1mol), (R)-1-naphthylethylamine (17.1g, 0.1mol) into anhydrous methanol (100mL), stir in ice-water bath for 2h, add cyano group three times Sodium borohydride (0.5mol), the molar ratio of the dosage for three times is 1:1:1, continue to stir for 2h, add dropwise 2mol / L hydrochloric acid (20mL) to quench the reaction, concentrate under reduced pressure, add 100mL of water to dilute, and Extract with ethyl acetate, separate the organic layer, add anhydrous sodium sulfate to dry, filter with suction, and concentrate under reduced pressure to obtain (R)-3-bromo-N-(1-(naphthalene-1-yl)ethyl)propan-1 - Amine (17.52 g, 0.06 mol), yield 60%.

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 present invention provides an intermediate compound and a preparation method for preparing cinacalcet hydrochloride. The intermediate compound has a structure shown in formula (I): wherein, X is selected from Br and Cl. The method for preparing cinacalcet hydrochloride uses 3-halopropanal and (R)-1-naphthylethylamine as starting compounds, and prepares cinacalcet hydrochloride through an intermediate compound formula (I). The method is simple, easy to obtain raw materials, environment-friendly, short in route, high in yield, good in purity and easy in industrialized production.

Description

technical field [0001] The invention relates to the field of medicine, in particular to an intermediate and a method for preparing cinacalcet hydrochloride. Background technique [0002] Cinacalcet is the first drug in a new class of compounds known as calcimimetics, which activate calcium receptors in the parathyroid glands, thereby reducing parathyroid hormone (PTH) secretion. The chemical name of cinacalcet hydrochloride is N-((1R)-1-(1-naphthyl)ethyl)-3-(3-(trifluoromethyl)phenyl)propan-1-amine hydrochloride , formula C 22 h 22 f 3 N HCl (CAS No.: 364782-34-3), also known as CNC-HCl, its structure is shown below: [0003] [0004] According to reports, the following methods are currently available for the preparation of cinacalcet hydrochloride: [0005] Scheme 1: Cinacalcet hydrochloride is prepared by reductive amination reaction, using m-trifluoromethyl phenylpropionaldehyde and R-1-(1-naphthyl)ethylamine as raw materials, and synthesized by titanium tetraisop...

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
Patent Type & Authority Patents(China)
IPC IPC(8): C07C209/60C07C211/30C07C209/74
CPCC07C209/60C07C209/74C07C211/30C07B2200/07
Inventor 廖艺李颜
Owner 廖艺
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

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

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com