Lersivirine

Base Information

• Chemical Name: Lersivirine
• CAS No.: 473921-12-9
• Molecular Formula: C17H18N4O2
• Molecular Weight: 310.356
• European Community (EC) Number: 638-819-6
• UNII: R3ZGC15A9A
• ChEMBL ID: CHEMBL571987
• DSSTox Substance ID: DTXSID0057881
• Metabolomics Workbench ID: 152769
• NCI Thesaurus Code: C83872
• Nikkaji Number: J2.807.839K
• Wikidata: Q27287760
• Mol file: 473921-12-9.mol

Synonyms:5-((3,5-diethyl-1-(2-hydroxyethyl)(3,5-14C2)-1H-pyrazol-4-yl)oxy)benzene-1,3-dicarbonitrile;lersivirine;UK 453,061;UK 453061;UK-453,061;UK-453061;UK453,061;UK453061

Chemical Property of Lersivirine

Chemical Property:

• Boiling Point: 455.382 °C at 760 mmHg
• PKA: 14.34±0.10(Predicted)
• Flash Point: 229.207 °C
• PSA: 94.86000
• Density: 1.192 g/cm³
• LogP: 2.53586
• Solubility.: Soluble in DMSO
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 310.14297583
• Heavy Atom Count: 23
• Complexity: 456

Purity/Quality:

99% ^*data from raw suppliers

Lersivirine（UK453061） >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC1=C(C(=NN1CCO)CC)OC2=CC(=CC(=C2)C#N)C#N
• Recent ClinicalTrials: A Long Term Safety Study Of Lersivirine For The Treatment Of HIV-1 Infection In Subjects Who Have Completed Treatment With Lersivirine In Studies A5271015 And A5271022
• Recent EU Clinical Trials: A LONG-TERM OPEN-LABEL EXTENSION STUDY OF LERSIVIRINE FOR THE TREATMENT OF HIV-1 INFECTION

Technology Process of Lersivirine

There total 7 articles about Lersivirine 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: 90.0%

zinc(II) cyanide (557-21-1) + 2-(4-(3,5-dibromophenoxy)-3,5-diethyl-1H-pyrazol-1-yl)ethan-1-ol → [14C]-Lersivirine (473921-12-9)

Guidance literature:

With [(2-di-tert-butylphosphino-2′,4′,6′-triisopropyl-1, 1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)] palladium(II) methanesulfonate; In tetrahydrofuran; water; at 40 ℃; Inert atmosphere;

DOI:10.1021/ol5032359

Reference yield: 71.0%

2-hydroxyethylhydrazine (109-84-2) + 5-(2-oxo-1-propanoylbutoxy)isophthalonitrile (473924-01-5) → [14C]-Lersivirine (473921-12-9)

Guidance literature:

With acetic acid;

DOI:10.1016/j.bmcl.2009.08.080

Reference yield:

3,5-dibromophenol (626-41-5) → [14C]-Lersivirine (473921-12-9)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / acetone / 2 h / 50 °C

2: acetic acid / 3 h / 50 °C / Sealed tube

3: [(2-di-tert-butylphosphino-2′,4′,6′-triisopropyl-1, 1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)] palladium(II) methanesulfonate / tetrahydrofuran; water / 40 °C / Inert atmosphere

With [(2-di-tert-butylphosphino-2′,4′,6′-triisopropyl-1, 1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)] palladium(II) methanesulfonate; potassium carbonate; acetic acid; In tetrahydrofuran; water; acetone;

DOI:10.1021/ol5032359

upstream raw materials:

2-hydroxyethylhydrazine

5-(2-oxo-1-propanoylbutoxy)isophthalonitrile

zinc(II) cyanide

3,5-heptanedione