1393813-43-8

Basic information

• Product Name: SulfaMide, N-[5-(4-broMophenyl)-6-(2-hydroxyethoxy)-4-pyriMidinyl]-N'-propyl-
• Synonyms: SulfaMide, N-[5-(4-broMophenyl)-6-(2-hydroxyethoxy)-4-pyriMidinyl]-N'-propyl-;N-[5-(4-Bromophenyl)-6-(2-hydroxyethoxy)-4-pyrimidinyl]-N'-propylsulfamide;N-(5-(4-bromophenyl)-6-(2-hydroxyethoxy)pyrimidin-4-yl)propane-1-sulfamide;N-[5-(4-Bromphenyl)-6-(2-hydroxyethoxy)pyrimidin-4-yl]-N'-propylsulfamid
• CAS NO: 1393813-43-8
• Molecular Formula: C₁₅H₁₉BrN₄O₄S
• Molecular Weight: 431.30476
• Mol File: 1393813-43-8.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 572.2±60.0 °C(Predicted)
• Appearance: /
• Density: 1.553±0.06 g/cm3(Predicted)
• PKA: 5.01±0.50(Predicted)
• CAS DataBase Reference: SulfaMide, N-[5-(4-broMophenyl)-6-(2-hydroxyethoxy)-4-pyriMidinyl]-N'-propyl-(CAS DataBase Reference)
• NIST Chemistry Reference: SulfaMide, N-[5-(4-broMophenyl)-6-(2-hydroxyethoxy)-4-pyriMidinyl]-N'-propyl-(1393813-43-8)
• EPA Substance Registry System: SulfaMide, N-[5-(4-broMophenyl)-6-(2-hydroxyethoxy)-4-pyriMidinyl]-N'-propyl-(1393813-43-8)

Safety Data

• Hazardous Substances Data: 1393813-43-8(Hazardous Substances Data)

Usage

Description

SulfaMide, N-[5-(4-bromophenyl)-6-(2-hydroxyethoxy)-4-pyrimidinyl]-N'-propylis a chemical compound with a specific molecular structure that features a pyrimidinyl core, a bromophenyl group, a hydroxyethoxy group, and a propyl chain. SulfaMide, N-[5-(4-broMophenyl)-6-(2-hydroxyethoxy)-4-pyriMidinyl]-N'-propylis characterized by its unique chemical properties and potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
SulfaMide, N-[5-(4-bromophenyl)-6-(2-hydroxyethoxy)-4-pyrimidinyl]-N'-propylis used as an impurity in the production of Macitentan (M105005), which is a dual, orally active, and potent endothelin receptor antagonist. Macitentan is primarily used for the treatment of pulmonary arterial hypertension, a severe lung disease characterized by high blood pressure in the arteries of the lungs.
The compound's role as an impurity in Macitentan production highlights its importance in the pharmaceutical industry, as it may affect the drug's efficacy, safety, and overall quality. Understanding and controlling the presence of this impurity can contribute to the development of more effective and safer treatments for pulmonary arterial hypertension.

Upstream product

• 1878-68-8 2-(4-bromophenyl)-acetic acid 
• 41841-16-1 (4-bromo-phenyl)-acetic acid methyl ester 
• 149506-35-4 2-(4-bromophenyl)-malonic acid dimethyl ester 
• 706811-25-8 5-(4-bromophenyl)-4,6-dihydroxypyrimidine 
• 146533-41-7 5-(4-bromophenyl)-4,6-dichloropyrimidine 
• 1393813-42-7 N-5-(4-bromophenyl)-6-chloro-4-pyrimidinyl-N‘-propylsulfamide 
• 107-21-1 ethylene glycol 
• 7580-85-0 tert-butyl glycidyl ether 

Downstream Products

• 2211059-05-9 2‐((6‐amino‐5‐(4‐bromophenyl)pyrimidin‐4‐yl)oxy)ethan‐1‐ol 
• 1433875-21-8 ACT-080803 

Relevant articles and documents

Characterization of degradation products of macitentan under various stress conditions using liquid chromatography/mass spectrometry

Rationale: Stress testing of a drug candidate is an important step in the drug discovery and development process. The presence of degradation products in a drug affects the quality as well as the safety and efficacy of drug formulation. Hence, it is essential to develop an efficient analytical method which could be useful for the separation, identification and characterization of all possible degradation products (DPs) of a drug. Macitentan (MT) is an endothelin receptor antagonist (ERA) drug used to treat high blood pressure in the lungs. Comprehensive stress testing of MT was carried out as per ICH guidelines to understand the degradation profile of the drug. Methods: MT was subjected to various stress conditions such as acidic, basic, neutral hydrolysis, oxidation, photolysis and thermal conditions; and the resulting degradation products were investigated using liquid chromatography/diode-array detection/electrospray ionization high-resolution mass spectrometry (LC/DAD/ESI-HRMS) and tandem mass spectrometry (MS/MS) techniques. An efficient and simple ultra-high-performance liquid chromatography (UHPLC) method has been developed using an Accucore C18 column (4.6?×?150?mm, 2.6?μm) using a gradient elution of 5?mM ammonium formate and acetonitrile as mobile phases. Results: MT was found to degrade under acid and base hydrolysis stress conditions; whereas it was stable under oxidation, neutral hydrolysis, thermal and photolytic conditions. MT formed nine DPs (DP1 to DP9) and one DP (DP10) under acidic and basic hydrolytic conditions, respectively. All the degradation products (DP1 to DP10) were identified and characterized by LC/MS/MS in positive ion mode with accurate mass measurements. Conclusions: MT was found to be labile under hydrolytic conditions. The structures of the DPs were characterized by appropriate mechanisms. The proposed method can be effectively used for the characterization of MT and its DPs.

Improved and single-pot process for the synthesis of macitentan, an endothelin receptor antagonist, via lithium amide-mediated nucleophilic substitution

Abstract: An improved, simple, efficient, and telescoped synthesis of macitentan, an endothelin receptor antagonist, starting from 5-(4-bromophenyl)-4,6-dichloropyrimidine in an overall yield of around 62% is described. Graphical abstract: [Figure not available: see fulltext.].

AN IMPROVED PROCESS FOR THE PREPARATION OF MACITENTAN

The present invention relates to an improved process for the preparation of macitentan and pharmaceutical acceptable salts thereof. Further present invention also relates to methylene chloride solvate of macitentan and their use in the preparation of pure macitentan.