GLPG0492 (R enantiomer)

Base Information

• Chemical Name: GLPG0492 (R enantiomer)
• CAS No.: 1215085-93-0
• Molecular Formula: C₁₉H₁₄F₃N₃O₃
• Molecular Weight: 389.334
• Mol file: 1215085-93-0.mol

Synonyms:(R)-(+)-4-[2,5-dioxo-4-(hydroxymethyl)-3-methyl-4-phenylimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile

Chemical Property of GLPG0492 (R enantiomer)

Chemical Property:

• Boiling Point: 544.0±60.0 °C(Predicted)
• PKA: 13.50±0.10(Predicted)
• Density: 1.50±0.1 g/cm3(Predicted)

Purity/Quality:

99.99%HPLC ^*data from raw suppliers

GLPG0492Renantiomer 98+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of GLPG0492 (R enantiomer)

There total 5 articles about GLPG0492 (R enantiomer) 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: 48.0%

4-[2,5-dioxo-4-(hydroxymethyl)-3-methyl-4-phenylimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile (1215085-63-4) → (R)-(+)-4-[2,5-dioxo-4-(hydroxymethyl)-3-methyl-4-phenylimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile (1215085-93-0) + GLPG0492 (1215085-92-9)

Guidance literature:

With Chiralcel OD; In n-heptane; isopropyl alcohol; Resolution of racemate;

DOI:10.1021/jm300281x

Reference yield:

5-phenyl-5-(2-propenyloxy)methylimidazolidine-2,4-dione (1215085-65-6) → (R)-(+)-4-[2,5-dioxo-4-(hydroxymethyl)-3-methyl-4-phenylimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile (1215085-93-0) + GLPG0492 (1215085-92-9)

Guidance literature:

Multi-step reaction with 4 steps

1: copper(I) oxide / N,N-dimethyl acetamide / 3 h / 160 °C / Inert atmosphere

2: potassium carbonate / N,N-dimethyl-formamide / 4 h / 20 °C / Inert atmosphere

3: boron dimethyl-trifluoro sulphide / dichloromethane / 4 h / 20 °C / Inert atmosphere

4: Chiralcel OD / n-heptane; isopropyl alcohol / Resolution of racemate

With copper(I) oxide; boron dimethyl-trifluoro sulphide; potassium carbonate; In n-heptane; dichloromethane; N,N-dimethyl acetamide; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/jm300281x

Reference yield:

4-[2,5-dioxo-4-phenyl-4-[(2-propenyloxy)methyl]imidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile (1215085-66-7) → (R)-(+)-4-[2,5-dioxo-4-(hydroxymethyl)-3-methyl-4-phenylimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile (1215085-93-0) + GLPG0492 (1215085-92-9)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 20 °C / Inert atmosphere

2: boron dimethyl-trifluoro sulphide / dichloromethane / 4 h / 20 °C / Inert atmosphere

3: Chiralcel OD / n-heptane; isopropyl alcohol / Resolution of racemate

With boron dimethyl-trifluoro sulphide; potassium carbonate; In n-heptane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/jm300281x

upstream raw materials:

4-[2,5-dioxo-4-(hydroxymethyl)-3-methyl-4-phenylimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile

4-bromo-2-(trifluoromethyl)benzonitrile

5-phenyl-5-(2-propenyloxy)methylimidazolidine-2,4-dione

4-[2,5-dioxo-4-phenyl-4-[(2-propenyloxy)methyl]imidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile

Refernces

• 1、 -. "NOVEL IMIDAZOLIDINE COMPOUNDS AS ANDROGEN RECEPTOR MODULATORS". Page/Page column 51. . Retrieved 2010/04/06.