Darapladib

Base Information

• Chemical Name: Darapladib
• CAS No.: 356057-34-6
• Molecular Formula: C36H38F4N4O2S
• Molecular Weight: 666.771133
• European Community (EC) Number: 619-937-7
• UNII: UI1U1MYH09
• DSSTox Substance ID: DTXSID70189073
• Nikkaji Number: J2.011.567J,J2.802.528I
• Wikipedia: Darapladib
• Wikidata: Q5222103
• NCI Thesaurus Code: C72985
• Pharos Ligand ID: 79KWZKX9DDDM
• Metabolomics Workbench ID: 149735
• ChEMBL ID: CHEMBL204021
• Mol file: 356057-34-6.mol

Synonyms:darapladib;N-(2-(diethylamino)ethyl)-2-(2-((4-fluorobenzyl)sulfanyl)-4-oxo-4,5,6,7-tetrahydro-1H-cyclopentapyrimidin-1-yl)-N-((4'-(trifluoromethyl)biphenyl-4-yl)methyl)acetamide;SB-480848

Chemical Property of Darapladib

Chemical Property:

• Boiling Point: 741.002 °C at 760 mmHg
• PKA: 9.03±0.10(Predicted)
• Flash Point: 401.944 °C
• PSA: 83.74000
• Density: 1.259 g/cm³
• LogP: 7.21980
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility.: ≥32.95 mg/mL in DMSO; insoluble in H2O; ≥891 mg/mL in EtOH
• XLogP3: 7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 13
• Exact Mass: 666.26516029
• Heavy Atom Count: 47
• Complexity: 1120

Purity/Quality:

98%,99%, ^*data from raw suppliers

Darapladib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)CCN(CC1=CC=C(C=C1)C2=CC=C(C=C2)C(F)(F)F)C(=O)CN3C4=C(CCC4)C(=O)N=C3SCC5=CC=C(C=C5)F
• Recent ClinicalTrials: Integrated Biomarker And Imaging Study - 2
• Recent EU Clinical Trials: A phase 2, multi-national, multi-centre, double masked,
• Description: Darapladib (SB-480848) is a reversible lipoprotein-associated phospholipase A2 (Lp-PLA2) inhibitor with IC50 of 0.25 nM. Phase 3.
• Uses: Treatment of atherosclerosis. Darapladib (SB-480848) is a reversible lipoprotein-associated phospholipase A2 (Lp-PLA2) inhibitor.

Technology Process of Darapladib

There total 16 articles about Darapladib 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: 82.63%

N,N-diethyl-N'-(4'-trifluoromethylbiphenyl-4-ylmethyl)ethane-1,2-diamine (304694-40-4) + {2-[(4-fluorobenzyl)sulfanyl]-4-oxo-4,5,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-1-yl}acetic acid (356058-42-9) → N-[2-(diethylamino)ethyl]-2-(2-{[(4-fluorophenyl)methyl]thio}-4-oxo-4,5,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-1-yl)-N-{[4’-(trifluoromethyl)-4-biphenylyl]methyl}acetamide (356057-34-6)

Guidance literature:

With boric acid; In toluene; at 110 ℃; for 6h; Reagent/catalyst; Temperature; Solvent;

Reference yield: 63.5%

→ N-[2-(diethylamino)ethyl]-2-(2-{[(4-fluorophenyl)methyl]thio}-4-oxo-4,5,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-1-yl)-N-{[4’-(trifluoromethyl)-4-biphenylyl]methyl}acetamide (356057-34-6)

Guidance literature:

Reference yield:

C19H17FN4O2S (1349902-21-1) + N,N-diethyl-N'-(4'-trifluoromethylbiphenyl-4-ylmethyl)ethane-1,2-diamine (304694-40-4) → N-[2-(diethylamino)ethyl]-2-(2-{[(4-fluorophenyl)methyl]thio}-4-oxo-4,5,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-1-yl)-N-{[4’-(trifluoromethyl)-4-biphenylyl]methyl}acetamide (356057-34-6)

Guidance literature:

In isobutyl methyl ether; at 92 ℃; Industry scale;

upstream raw materials:

N,N-diethyl-N'-(4'-trifluoromethylbiphenyl-4-ylmethyl)ethane-1,2-diamine

{2-[(4-fluorobenzyl)sulfanyl]-4-oxo-4,5,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-1-yl}acetic acid

2-ethoxycarbonyl-1-cyclopentanone

2-mercapto-1,5,6,7-tetrahydro-cyclopentapyrimidin-4-one

Refernces

• 1、 Guibbal, Florian,Bénard, Sébastien,Patché, Jessica,Meneyrol, Vincent,Couprie, Jo?l,Yong-Sang, Jennyfer,Meilhac, Olivier,Jestin, Emmanuelle. "Regioselectivity of thiouracil alkylation: Application to optimization of Darapladib synthesis". supporting information. p. 787 - 792. Retrieved 2018/01/17.
• 2、 -. "PROCESSES FOR THE PREPARATION OF DARAPLADIB AND ITS INTERMEDIATES". Page/Page column 19; 20. . Retrieved 2015/06/25.