293738-17-7

Basic information

• Product Name: N-[2-(2-methoxyphenoxy)ethyl]acetamide
• CAS NO: 293738-17-7
• Molecular Weight: 209.245
• Mol File: 293738-17-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-[2-(2-methoxyphenoxy)ethyl]acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[2-(2-methoxyphenoxy)ethyl]acetamide(293738-17-7)
• EPA Substance Registry System: N-[2-(2-methoxyphenoxy)ethyl]acetamide(293738-17-7)

Safety Data

• Hazardous Substances Data: 293738-17-7(Hazardous Substances Data)

Usage

Description

N-[2-(2-methoxyphenoxy)ethyl]acetamide is an organic compound that serves as a crucial building block in the synthesis of Carvedilol, a medication with antihypertensive properties.

Uses

Used in Pharmaceutical Industry:
N-[2-(2-methoxyphenoxy)ethyl]acetamide is used as a key intermediate in the synthesis of Carvedilol (C184625) for its antihypertensive properties. Carvedilol, a nonselective β-adrenergic blocker with α1-blocking activity, is utilized in the treatment of congestive heart failure, making this compound an essential component in cardiovascular medicine.

Upstream product

• 1836-62-0 2-(2-methoxy-phenoxy)-ethylamine 
• 108-24-7 acetic anhydride 
• 1120-64-5 2-methyl-4,5-dihydro-1,3-oxazole 
• 90-05-1 2-methoxy-phenol 

Relevant articles and documents

Hybridization of β-Adrenergic Agonists and Antagonists Confers G Protein Bias

Starting from the β-adrenoceptor agonist isoprenaline and beta-blocker carvedilol, we designed and synthesized three different chemotypes of agonist/antagonist hybrids. Investigations of ligand-mediated receptor activation using bioluminescence resonance energy transfer biosensors revealed a predominant effect of the aromatic head group on the intrinsic activity of our ligands, as ligands with a carvedilol head group were devoid of agonistic activity. Ligands composed of a catechol head group and an antagonist-like oxypropylene spacer possess significant intrinsic activity for the activation of Gαs, while they only show weak or even no β-arrestin-2 recruitment at both β1- and β2-AR. Molecular dynamics simulations suggest that the difference in G protein efficacy and β-arrestin recruitment of the hybrid (S)-22, the full agonist epinephrine, and the β2-selective, G protein-biased partial agonist salmeterol depends on specific hydrogen bonding between Ser5.46 and Asn6.55, and the aromatic head group of the ligands.

METHOD FOR PREPARING 2-ALKOXYPHENOXYETHANAMINES FROM 2-ALKOXYPHENOXYETHYLACETAMIDES

The present invention relates to a method for preparing 2-Alkoxyphenoxyethanamines and more particularly relates to the preparation of the new chemical entity 2-Alkoxyphenoxyethylacetamides, in particular as intermediates in said method. An industrial process for the synthesis of 2-Alkoxyphenoxyethanamines which is cheap and easy to perform, is a long felt need for those skilled in the art. The object of the present invention is therefore to provide a process for the industrial production of phenoxyethanamine which is cheap and easy to perform. This object is solved by the new chemical entity 2-Alkoxyphenoxyacetamide which is prepared by reacting an ortho substituted phenol with a 2-Alkyloxazoline. By hydrolysis of the acetamide with water in the presence of organic or mineral acids such as hydrochloric acid and/or sulfuric acid, the 2-Alkylphenoxyethanamine is obtained.