Darapladib-iMpurity

Base Information

• Chemical Name: Darapladib-iMpurity
• CAS No.: 1389264-17-8
• Molecular Formula: C₃₆H₃₈F₄N₄O₂S
• Molecular Weight: 666.783
• Mol file: 1389264-17-8.mol

Synonyms:Darapladib-iMpurity;N-(2-(Diethylamino)ethyl)-2-((2-((4-fluorobenzyl)thio)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)oxy)-N-((4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)methyl)acetamide

Chemical Property of Darapladib-iMpurity

Chemical Property:

• Boiling Point: 766.5±60.0 °C(Predicted)
• PKA: 9.02±0.10(Predicted)
• Density: 1.31±0.1 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

97% ^*data from raw suppliers

Darapladib-impurity ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Darapladib-iMpurity

There total 8 articles about Darapladib-iMpurity 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: 80.0%

2-((2-((4-fluorobenzyl)thio)-6,7-dihydro-5H-cyclopenta[d]pyrimi din-4-yl)oxy)acetic acid + N,N-diethyl-N'-(4'-trifluoromethylbiphenyl-4-ylmethyl)ethane-1,2-diamine (304694-40-4) → darapladib (1389264-17-8)

Guidance literature:

2-((2-((4-fluorobenzyl)thio)-6,7-dihydro-5H-cyclopenta[d]pyrimi din-4-yl)oxy)acetic acid; N,N-diethyl-N'-(4'-trifluoromethylbiphenyl-4-ylmethyl)ethane-1,2-diamine; With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.166667h;

With 1-[(1-(cyano-?2-?ethoxy-?2-?oxoethylidenaminooxy)?dimethylamino-?morpholino)]-uronium hexafluorophosphate; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 6h;

DOI:10.1016/j.bmcl.2017.12.052

Reference yield:

2-sulfanylidene-1,2,3,4,6,7-hexahydro-5H-cyclopenta[d]pyrimidin-4-one (35563-27-0) → darapladib (1389264-17-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium carbonate; potassium iodide / acetone / 3 h / 54 °C

2.1: potassium carbonate / N,N-dimethyl-formamide / 18 h / 75 °C / Inert atmosphere

3.1: trifluoroacetic acid / dichloromethane / 18 h / 20 °C / Inert atmosphere

4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / 20 °C

4.2: 6 h / 0 - 20 °C

With potassium carbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; potassium iodide; In dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.bmcl.2017.12.052

Reference yield:

methyl 2-oxocyclopentane-1-carboxylate (10472-24-9,265317-94-0) → darapladib (1389264-17-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 16 h / 82 °C

2.1: potassium carbonate; potassium iodide / acetone / 3 h / 54 °C

3.1: potassium carbonate / N,N-dimethyl-formamide / 18 h / 75 °C / Inert atmosphere

4.1: trifluoroacetic acid / dichloromethane / 18 h / 20 °C / Inert atmosphere

5.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / 20 °C

5.2: 6 h / 0 - 20 °C

With potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; potassium iodide; In dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1016/j.bmcl.2017.12.052

upstream raw materials:

2-sulfanylidene-1,2,3,4,6,7-hexahydro-5H-cyclopenta[d]pyrimidin-4-one

2-[(4-fluorobenzyl)sulfanyl]-1,5,6,7-tetrahydro-4H-cyclopenta[d]pyrimidin-4-one

4-(4-trifluoromethylphenyl)benzaldehyde

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

Refernces