Darusentan

Base Information

• Chemical Name: Darusentan
• CAS No.: 171714-84-4
• Deprecated CAS: 177036-80-5
• Molecular Formula: C22H22N2O6
• Molecular Weight: 410.426
• European Community (EC) Number: 605-614-8
• UNII: 33JD57L6RW
• DSSTox Substance ID: DTXSID1057664
• Nikkaji Number: J847.578D
• Wikipedia: Darusentan
• Wikidata: Q5225810
• NCI Thesaurus Code: C75991
• Pharos Ligand ID: 7ZUAD1YRXBA3
• Metabolomics Workbench ID: 149313
• ChEMBL ID: CHEMBL23261
• Mol file: 171714-84-4.mol

Synonyms:(+)-(S)-2-((4,6-dimethoxy-2-pyrimidinyl)oxy)-3-methoxy-3,3-diphenylpropionic acid;2-(4,6-dimethoxypyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropionic acid;benzenepropanoic acid, alpha-((4,6-dimethoxy-2-pyrimidinyl)oxy)-beta-methoxy-beta-phenyl-, (S)-;darusentan;LU 127043;LU 135252;LU-135252

Chemical Property of Darusentan

Chemical Property:

• Vapor Pressure: 1.23E-14mmHg at 25°C
• Refractive Index: 1.583
• Boiling Point: 587.307 °C at 760 mmHg
• PKA: 1.82±0.10(Predicted)
• Flash Point: 308.993 °C
• PSA: 100.00000
• Density: 1.269 g/cm³
• LogP: 2.91600
• Storage Temp.: 2-8°C
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 410.14778643
• Heavy Atom Count: 30
• Complexity: 506

Purity/Quality:

98%Min ^*data from raw suppliers

S-Darusentan >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=NC(=N1)OC(C(=O)O)C(C2=CC=CC=C2)(C3=CC=CC=C3)OC)OC
• Isomeric SMILES: COC1=CC(=NC(=N1)O[C@H](C(=O)O)C(C2=CC=CC=C2)(C3=CC=CC=C3)OC)OC
• Recent ClinicalTrials: Darusentan Effect on PET Uptake Heterogeneity
• Recent EU Clinical Trials: DORADO-AC-EX – A Double-Blind, Active-Controlled, Long-Term Safety Extension Study to the Phase 3 DORADO-AC Study (Protocol DAR-312) of Darusentan in Resistant Hypertension

Technology Process of Darusentan

There total 12 articles about Darusentan 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: 86.53%

(S)-methyl 2-(4,6-dimethoxypyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropionate (177036-79-2) → darusentan (171714-84-4)

Guidance literature:

With water; sodium hydroxide; In 1,4-dioxane; at 40 - 45 ℃; for 30h;

Reference yield: 85.0%

(S)-1-[p-chlorophenyl]ethylammonium-(S)-2-hydroxy-3-methoxy-3,3-diphenylpropionate (264123-18-4) + 4,6-dimethoxypyrimidin-2-yl methyl sulfone (113583-35-0) → darusentan (171714-84-4)

Guidance literature:

With lithium amide; In N,N-dimethyl-formamide; at 20 - 30 ℃; for 16h; Large scale;

DOI:10.1021/op000040n

Reference yield:

(2S)-2-(4,6-dimethoxypyrimidin-2-yloxy)-3-methoxy-3,3-diphenyl ethyl propionate → darusentan (171714-84-4)

Guidance literature:

With water; sodium hydroxide; In 1,4-dioxane; at 80 ℃; for 8h;

upstream raw materials:

(S)-methyl 2-(4,6-dimethoxypyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropionate

benzophenone

(S)-2-hydroxy-3-methoxy-3,3-diphenylpropionic acid

2-hydroxy-3-methoxy-3,3-diphenylpropionicacid methyl ester

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF AN ENDOTHELIN RECEPTOR ANTAGONIST". Page/Page column 23. . Retrieved 2013/05/09.
• 2、 -. "IMPROVED PROCESS FOR THE PREPARATION OF ENDOTHELIN RECEPTOR ANTAGONISTS". Page/Page column 23-24. . Retrieved 2010/08/05.