N-[6-Chloro-5-(2-methoxyphenoxy)[2,2'-bipyrimidin]-4-yl]-4-(1,1-dimethylethyl)benzenesulfonamide potassium salt

Base Information

• Chemical Name: N-[6-Chloro-5-(2-methoxyphenoxy)[2,2'-bipyrimidin]-4-yl]-4-(1,1-dimethylethyl)benzenesulfonamide potassium salt
• CAS No.: 301646-59-3
• Molecular Formula: C25H23ClN5O4S^.K
• Molecular Weight: 564.10
• Mol file: 301646-59-3.mol

Synonyms:Benzenesulfonamide,N-[6-chloro-5-(2-methoxyphenoxy)[2,2'-bipyrimidin]-4-yl]-4-(1,1-dimethylethyl)-,potassium salt (9CI);

Chemical Property of N-[6-Chloro-5-(2-methoxyphenoxy)[2,2'-bipyrimidin]-4-yl]-4-(1,1-dimethylethyl)benzenesulfonamide potassium salt

Chemical Property:

• PSA: 112.54000
• LogP: 7.16030

Purity/Quality:

97% ^*data from raw suppliers

Potassium ((4-(tert-butyl)phenyl)sulfonyl)(6-chloro-5-(2-methoxyphenoxy)-[2,2'-bipyrimidin]-4-yl)amide 95+% ^*data from reagent suppliers

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MSDS Files:

SDS file from LookChem

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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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