150727-06-3

Basic information

• Product Name: 4-tert-Butyl-N-(6-chloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamide
• Synonyms: N-[6-CHLORO-5-(2-METHOXYPHENOXY)-(2,2-BIPYRIMIDINE)4-4-YL]-(1,1-DIMETHYLETHYL)-BENZENESULFONAMIDE;4-tert-Butyl-N-(6-chloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamide;n-[6-chloro-5-(2-methoxyphenoxy)[2,2'-bipyrimidin]-4-yl]-4-(1,1-dimethylethyl)benzenesulfonamide;Benzenesulfonamide, N-[6-chloro-5-(2-methoxyphenoxy)[2,2'-bipyrimidin]-4-yl]-4-(1,1-dimethylethyl)-;N-[6-chloro-5-(2-methoxyphenoxy)[2,2'-bipyrimidin]-4-yl]-4-(1,1-dimethylethyl)-B;Benzenesulfonamide, N-[6-chloro-5-(2-methoxyphenoxy)[2,2'-bipyrimidin]-4-yl]-4-(1,1-dimethylethyl)- (bosentan intermediate);Benzenesulfonamide, N-[6-Chloro-5-(2-Methoxyphenoxy)[2,2'-Bi-Pyrimidin]-4-Yl]-4-(1,1-Dimethylethyl)-(9ci);4-tert-Butyl-N-[6-chloro-5-(2-methoxyphenoxy)-2-(2
• CAS NO: 150727-06-3
• Molecular Formula: C₂₅H₂₄ClN₅O₄S
• Molecular Weight: 526.01
• EINECS: 1312995-182-4
• Product Categories: pyrimidine;Bases & Related Reagents;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals
• Mol File: 150727-06-3.mol
• Article Data: 24

Chemical Properties

• Melting Point: 212-214°C
• Boiling Point: 680.199 °C at 760 mmHg
• Flash Point: 365.171 °C
• Appearance: light pale yellow sold
• Density: 1.366 g/cm³
• Storage Temp.: -20?C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 3.67±0.10(Predicted)
• CAS DataBase Reference: 4-tert-Butyl-N-(6-chloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-tert-Butyl-N-(6-chloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamide(150727-06-3)
• EPA Substance Registry System: 4-tert-Butyl-N-(6-chloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamide(150727-06-3)

Safety Data

• Hazardous Substances Data: 150727-06-3(Hazardous Substances Data)

Usage

Description

4-tert-Butyl-N-(6-chloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamide is a complex organic compound with a unique chemical structure. It is characterized by its light pale yellow solid appearance and serves as an intermediate in the synthesis of Bosentan, a mixed endothelin receptor antagonist. 4-tert-Butyl-N-(6-chloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamide plays a crucial role in the pharmaceutical industry due to its involvement in the production of Bosentan, which has significant therapeutic applications.

Uses

1. Pharmaceutical Industry:
4-tert-Butyl-N-(6-chloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamide is used as an intermediate in the synthesis of Bosentan for its role as a mixed endothelin receptor antagonist. Bosentan is prescribed for the treatment of pulmonary arterial hypertension and digital ulcers associated with systemic sclerosis. The compound's ability to block the action of endothelin, a potent vasoconstrictor, makes it a valuable asset in managing these conditions.
2. Quality Control and Regulatory Compliance:
4-tert-Butyl-N-(6-chloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamide is also used as an intermediate for Bosentan USP Related Compound A. This application is essential for ensuring the quality, safety, and efficacy of Bosentan as a pharmaceutical product. By using this compound as a reference, manufacturers can verify the identity, purity, and strength of Bosentan, adhering to the United States Pharmacopeia (USP) standards.

Upstream product

• 150728-13-5 4,6-dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidine 
• 90-05-1 2-methoxy-phenol 
• 150726-89-9 (2-methoxyphenoxy)-malonic acid dimethyl ester 
• 14080-23-0 2-cyanopyrimidine 
• 329923-17-3 5-(2-methoxyphenoxy)-2-(pyrimidin-2-yl)tetrahydropyrimidine-4,6-dione 
• 42839-08-7 pyrimidine-2-carboxylic acid ethyl ester 
• 6292-59-7 4-tert-butylbenzenesulphonamide 
• 1268612-27-6 C₁₅H₁₁ClN₄O₃ 
• 20730-58-9 2-(2-Methoxyphenoxy)propanedioic acid diethyl ester 
• 329923-15-1 4,6-dihydroxy-5-(o-methoxyphenoxy)-2-(2-pyrimidinyl)-pyrimidine 
• 150728-12-4 5-(2-methoxyphenoxy)-2-(pyrimidin-2-yl) pyrimidine-4,6(1H, 5H)-dione 
• 57871-18-8 methyl ester of imino-pyrimidine acid 

Downstream Products

• 147536-97-8 bosentan 
• 1065472-77-6 d4-4-tert-butyl-N-[6-(2-hydroxy-ethoxy)-5-(2-methoxy-phenoxy)-[2,2']bipyrimidinyl-4-yl]-benzenesulfonamide 
• 174227-14-6 p-tert-butyl-N-[6-hydroxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzenesulfonamide 
• 1174918-31-0 bosentan potassium 
• 1448588-52-0 N,N′-(6,6′-(2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis-(methylene)bis(oxy)bis(5-(2-methoxy phenoxy)-2,2′-bipyrimidine-6,4-diyl))bis(4-tert-butylbenzenesulfonamide) 
• 1448588-53-1 N,N′-(6,6′-(2,3-dihydroxybutane-1,4-diyl)bis(oxy)bis-(5-(2-methoxyphenoxy)-2,2′-bipyrimidine-6,4-diyl))bis-(4-tert-butylbenzenesulfonamide) 
• 1632289-55-4 4-tert-butyl-N-[6-(2,3-dihydroxypropoxy)-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl]benzenesulfonamide 
• 1632289-54-3 4-tert-butyl-N-{6-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl}benzenesulfonamide 
• 157212-55-0 bosentan monohydrate 
• 346672-40-0 4-tert.-butyl-N-[6-(4-(3-methoxybenzyloxy)-2-butynyloxy)-5-(o-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzene sulfonamide 
• 346672-39-7 4-tert.-butyl-N-[6-(4-(4-methylbenzyloxy)-2-butynyloxy)-5-(o-methoxy-phenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzene sulfonamide 
• 346671-46-3 4-tert.-butyl-N-[6-(4-hydroxy-2-butynyloxy)-5-(o-methoxyphenoxy)-2-(2-pyrimidinyl)4-pyrimidinyl]benzene sulfonamide 

Relevant articles and documents

Improved procedure for the preparation of Bosentan, an endothelin receptor antagonist

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Metabolism study and biological evaluation of bosentan derivatives

Bosentan, the first-in-class drug used in treatment of pulmonary arterial hypertension, is principally metabolized by the cytochromes P450, and it is responsible for cytochromes induction and drug-drug interaction events with moderate to severe consequences. A strategy to reduce drug-drug interactions consists of increasing the metabolic stability of the perpetrator, and fluorinated analogues are often designed to block the major sites of metabolism. In this paper bosentan analogues were synthesized, and their metabolism and biological activity were evaluated. All synthesized compounds showed an improved metabolic stability towards CYP2C9, with one maintaining a moderate antagonist effect towards the ETA receptor.

An alternate synthesis of bosentan monohydrate, an endothelin receptor antagonist 1

An alternate synthesis of an endothelin receptor antagonist bosentan monohydrate is reported. This new synthetic route involves the coupling of p-tert-butyl-N-[6-chloro-5-(2-methoxy-phenoxy)(2,2′-bipyrimidin)-4-yl] benzene sulfonamide with commercially available raw material (2,2-dimethyl-1,3-dioxolan-4-yl)methanol as the key step. Attractive features of this approach are its versatileness, commercial availability of raw materials, usage of eco-friendly reagents, and it efficiently provides the desired bosentan monohydrate free from reported impurities such as dimer, N-alkylated, and pyrimidinone impurities. Georg Thieme Verlag Stuttgart, New York.