Bosentan hydrate

Base Information

• Chemical Name: Bosentan hydrate
• CAS No.: 157212-55-0
• Molecular Formula: C₂₇H₂₉N₅O₆S*H₂O
• Molecular Weight: 569.638
• Hs Code.: 2935909550
• European Community (EC) Number: 620-486-3,691-652-0
• UNII: Q326023R30
• DSSTox Substance ID: DTXSID80873178
• Wikidata: Q27114267
• NCI Thesaurus Code: C47417
• RXCUI: 75207
• Metabolomics Workbench ID: 54376
• Mol file: 157212-55-0.mol

Synonyms:4-t-butyl-N-(6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamide;bosentan;bosentan anhydrous;bosentan monohydrate;Ro 47 0203;Ro 47-0203;Ro 470203;Ro-47-0203;Tracleer

Chemical Property of Bosentan hydrate

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 3.84E-23mmHg at 25°C
• Melting Point: 114-118 °C
• Boiling Point: 742.3 °C at 760 mmHg
• Flash Point: 402.8 °C
• PSA: 163.26000
• LogP: 5.29340
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Very Slightly, Heated)
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 11
• Exact Mass: 569.19441952
• Heavy Atom Count: 40
• Complexity: 839

Purity/Quality:

99%, ^*data from raw suppliers

BosentanHydrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC2=C(C(=NC(=N2)C3=NC=CC=N3)OCCO)OC4=CC=CC=C4OC.O
• Recent EU Clinical Trials: The Clinical Efficacy And Subclinical Effects on arterial STIFFNESS of bosentan therapy added to usual care in patients with systemic sclerosis with digital ulcers.
• General Description: Bosentan hydrate is an endothelin receptor antagonist primarily used to treat pulmonary hypertension, synthesized through an optimized process that avoids critical impurities, achieves high yields (50-55%), and ensures ICH-grade quality with polymorphic stability. The improved method employs commercially available reagents, simplified steps, and optimized conditions, such as acetonitrile as a solvent and NaOH as a base, followed by purification with ethyl acetate and methanol.

Technology Process of Bosentan hydrate

There total 9 articles about Bosentan hydrate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

ethylene glycol (107-21-1) + 4-tert-butyl-N-(6-chloro-5-(2-methoxyphenoxy)2,2'-bipyrimidin-4-yl)benzene sulfonamide (150727-06-3) → p-tert-butyl-N-[6-hydroxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzenesulfonamide (174227-14-6) + N,N'-(6,6''-(ethane-1,2-diylbis(oxy))bis(5-(2-methoxyphenoxy)-[2,2'-bipyrimidine]-6,4-diyl))bis(4-(tert-butyl)benzenesulfonamide) (1097263-60-9) + bosentan monohydrate (157212-55-0)

Guidance literature:

With sodium;

DOI:10.1080/00304948.2013.835222

Reference yield:

4-tert-butyl-N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzene sulfonamide potassium salt → bosentan monohydrate (157212-55-0)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydroxide

2: toluene; ethanol

3: sodium hydroxide / water; ethanol

With sodium hydroxide; In ethanol; water; toluene;

DOI:10.1080/00304948.2016.1234826

Reference yield:

C27H28N5O6S(1-)*H4N(1+) → bosentan monohydrate (157212-55-0)

Guidance literature:

With hydrogenchloride; In methanol; ethanol; water; acetonitrile;

DOI:10.1080/00304948.2016.1234826

upstream raw materials:

ethylene glycol

4-tert-butyl-N-(6-chloro-5-(2-methoxyphenoxy)2,2'-bipyrimidin-4-yl)benzene sulfonamide

4,6-dihydroxy-5-(o-methoxyphenoxy)-2-(2-pyrimidinyl)-pyrimidine

4,6-dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidine

Refernces

A new efficient synthetic process for an endothelin receptor antagonist, bosentan monohydrate

10.1021/op400100s

The study presents a novel and efficient synthetic process for bosentan monohydrate, an endothelin receptor antagonist used to treat pulmonary hypertension. The key innovation involves coupling p-tert-butyl-N-(6-chloro-5-(2-methoxy phenoxy)-2,2'-bipyrimidin-4-yl)benzenesulfonamide (7) with (2,2-dimethyl-1,3-dioxolane-4,5-diyl)dimethanol (14). This method eliminates the formation of critical impurities such as pyrimidinone 8, dimer impurity 9, and N-alkylated impurity 13, which are common in previous synthesis methods. The new process achieves an overall yield of 50-55%, corresponding to an average step yield of 85%, using simple steps and commercially available chemicals. The study also details the optimization of reaction conditions, such as the use of acetonitrile as a solvent and NaOH as a base, and the final purification of bosentan monohydrate using a combination of ethylacetate and methanol. The resulting bosentan monohydrate meets ICH-grade quality standards and exhibits polymorphic stability under various conditions.

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