174227-14-6

Basic information

• Product Name: BenzenesulfonaMide, N-[1,6-dihydro-5-(2-Methoxyphenoxy)-6-oxo[2,2'-bipyriMidin]-4-yl]-4-(1,1-diMethylethyl)-
• Synonyms: BenzenesulfonaMide, N-[1,6-dihydro-5-(2-Methoxyphenoxy)-6-oxo[2,2'-bipyriMidin]-4-yl]-4-(1,1-diMethylethyl)-;Bosentan USP RC B;Bosentan IMpurity D;Bosentan Related CoMpound B;N-[1,6-Dihydro-5-(2-methoxyphenoxy)-6-oxo[2,2'-bipyrimidin]-4-yl]-4-(1,1-dimethylethyl)benzenesulfonamide;Bosentan Related Compound B (15 mg) (4-(tert-butyl)-N-[6-hydroxy-5-(2-methoxyphenoxy)-(2,2'-bipyrimidin)-4-yl]benzenesulfonamide);O-Deshydroxyethyl Bosentan;Bosentan USP Related Compound B: 4-(tert-Butyl)-N-[6-hydroxy-5-(2-methoxyphenoxy)-(2,2'-bipyrimidin)-4-yl]benzenesulfonamide
• CAS NO: 174227-14-6
• Molecular Formula: C₂₅H₂₅N₅O₅S
• Molecular Weight: 507.5615
• Mol File: 174227-14-6.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: BenzenesulfonaMide, N-[1,6-dihydro-5-(2-Methoxyphenoxy)-6-oxo[2,2'-bipyriMidin]-4-yl]-4-(1,1-diMethylethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: BenzenesulfonaMide, N-[1,6-dihydro-5-(2-Methoxyphenoxy)-6-oxo[2,2'-bipyriMidin]-4-yl]-4-(1,1-diMethylethyl)-(174227-14-6)
• EPA Substance Registry System: BenzenesulfonaMide, N-[1,6-dihydro-5-(2-Methoxyphenoxy)-6-oxo[2,2'-bipyriMidin]-4-yl]-4-(1,1-diMethylethyl)-(174227-14-6)

Safety Data

• Hazardous Substances Data: 174227-14-6(Hazardous Substances Data)

Usage

Uses

O-Deshydroxyethyl Bosentan (Bosentan USP Related Compound B) is an impurity of Bosentan (B675900); a mixed endothelin receptor antagonist. Used as a vasodilator and antihypertensive.

Upstream product

• 150728-12-4 5-(2-methoxyphenoxy)-2-(pyrimidin-2-yl) pyrimidine-4,6(1H, 5H)-dione 
• 14080-23-0 2-cyanopyrimidine 
• 150726-89-9 (2-methoxyphenoxy)-malonic acid dimethyl ester 
• 57871-18-8 methyl ester of imino-pyrimidine acid 
• 90-05-1 2-methoxy-phenol 
• 329923-15-1 4,6-dihydroxy-5-(o-methoxyphenoxy)-2-(2-pyrimidinyl)-pyrimidine 
• 107-21-1 ethylene glycol 
• 150727-06-3 4-tert-butyl-N-(6-chloro-5-(2-methoxyphenoxy)2,2'-bipyrimidin-4-yl)benzene sulfonamide 
• 6292-59-7 4-tert-butylbenzenesulphonamide 
• 150728-13-5 4,6-dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidine 
• 7388-28-5 sodium 2-hydroxyethoxide 
• 147536-97-8 bosentan 

Downstream Products

• 147536-97-8 bosentan 
• 157212-55-0 bosentan monohydrate 
• 1174918-30-9 4-tert-butyl-N-(5-(2-methoxyphenoxy)-6-(2-oxoethoxy)-2,2′-bipyrimidin-4-yl)benzenesulfonamide 
• 180576-46-9 methyl 2-(6-(4-tert-butylphenylsulfonamido)-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yloxy)acetate 
• 1447959-38-7 4-tert-butyl-N-(6-(cyanomethoxy)-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl) benzenesulfonamide 

Relevant articles and documents

Improved Large-Scale Synthesis of Bosentan Monohydrate

-

New approaches to endothelin receptor antagonist-bosentan

An improved and efficient synthetic process developed for an endothelin receptor antagonist, bosentan monohydrate by condensing a key intermediate 4-tert-butyl-N-(6-hydroxy-5-(2-methoxyphenoxy)-2,2'-bipyrimidine-4-yl) benezenesulfonamide 5 with commercially cheaper chloro acetonitrile and α-halo esters. This synthetic approach efficiently provides highly pure bosentan without formation of the major impurity 2 (dimer) and less than 0.15% of Nalkylated impurity 3 and pyrimidinone impurity 5 in the final product. In the present process upon purification of bosentan monohydrate gave overall yield of 62-65%.

IMPROVED PROCESS FOR THE PREPARATION OF 4-(1,1-DIMETHYLETHYL)-N-[6-(2-HYDROXYETHOXY)-5-(2-METHOXYPHENOXY)[2,2'-BIPYRIMIDIN]-4-YL]BENZENESULFONAMIDE

The present invention relates to improved process for the preparation of 4-(1,1-dimethylethyl)-n-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy) [2,2'-bipyrimidin]-4-yl] benzene sulfonamide monohydrate. Formula (I)