[4-(3-Fluoro-5-trifluoromethylpyridin-2-yl)piperazin-1-yl][5-Methylsulfonyl-2-[((S)-2,2,2-trifluoro-1-methylethyl)oxy]phenyl]methanone

Base Information

• Chemical Name: [4-(3-Fluoro-5-trifluoromethylpyridin-2-yl)piperazin-1-yl][5-Methylsulfonyl-2-[((S)-2,2,2-trifluoro-1-methylethyl)oxy]phenyl]methanone
• CAS No.: 845614-11-1
• Molecular Formula: C21H20F7N3O4S
• Molecular Weight: 543.462
• Mol file: 845614-11-1.mol

Synonyms:[4-[3-fluoro-5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]-[5-methylsulfonyl-2-[(2S)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone; [4-(3-Fluoro-5-trifluoromethylpyridin-2-yl)piperazin-1-yl][5-Methylsulfonyl-2-[((S)-2,2,2-trifluoro-1-methylethyl)oxy]phenyl]methanone; [4-(3-fluoro-5-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-[5-methanesulfonyl-2-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-methanone; (S)-[4-(3-fluoro-5-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-[5-methanesulfonyl-2-(2,2,2-trifluoro-1-methyl-ethoxy)-phenyl]-methanone

Chemical Property of [4-(3-Fluoro-5-trifluoromethylpyridin-2-yl)piperazin-1-yl][5-Methylsulfonyl-2-[((S)-2,2,2-trifluoro-1-methylethyl)oxy]phenyl]methanone

Chemical Property:

• PSA: 88.19000
• Density: 1.444
• LogP: 5.01870
• Solubility.: insoluble in H2O; ≥17.94 mg/mL in EtOH; ≥88.9 mg/mL in DMSO with ultrasonic

Purity/Quality:

98%Min ^*data from raw suppliers

Bitopertin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Bitopertin is a potent and noncompetitive glycine reuptake inhibitor (GRI). Bitopertin is an investigational agent for the treatment of schizophrenia.

Technology Process of [4-(3-Fluoro-5-trifluoromethylpyridin-2-yl)piperazin-1-yl][5-Methylsulfonyl-2-[((S)-2,2,2-trifluoro-1-methylethyl)oxy]phenyl]methanone

There total 12 articles about [4-(3-Fluoro-5-trifluoromethylpyridin-2-yl)piperazin-1-yl][5-Methylsulfonyl-2-[((S)-2,2,2-trifluoro-1-methylethyl)oxy]phenyl]methanone 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: 78.0%

1-(3-fluoro-5-(trifluoromethyl)pyridin-2-yl)piperazine (845616-81-1) + 5-methane-sulfonyl-2-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-benzoic acid (845616-82-2,845616-83-3) → Bitopertin (845614-11-1)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/jm100210p

Reference yield: 36.0%

rac-[4-(3-fluoro-5-trifluoromethylpyridin-2-yl)piperazin-1-yl]-[5-methanesulfonyl-2-(2,2,2-trifluoro-1-methylethoxy)phenyl]-methanone → Bitopertin (845614-11-1) + [(R)-4-(3-fluoro-5-trifluoromethylpyridin-2-yl)piperazin-1-yl][5-methanesulfonyl-2-(2,2,2-trifluoro-1-methylethoxy)phenyl]methanone (845614-12-2)

Guidance literature:

With Chiralpack AD column; In n-heptane; isopropyl alcohol; under 11251.1 Torr; Resolution of racemate;

DOI:10.1021/jm100210p

Reference yield:

1-(3-fluoro-5-(trifluoromethyl)pyridin-2-yl)piperazine (845616-81-1) + C11H10ClF3O4S → Bitopertin (845614-11-1)

Guidance literature:

With triethylamine; In toluene; at 20 ℃; for 1 - 1.25h;

upstream raw materials:

1-(3-fluoro-5-(trifluoromethyl)pyridin-2-yl)piperazine

5-methane-sulfonyl-2-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-benzoic acid

2,3-dichloro-5-trifluoromethylpyridine

2,3-difluoro-5-(trifluoromethyl)pyridine

Refernces

• 1、 Pinard, Emmanuel,Alanine, Alexander,Alberati, Daniela,Bender, Markus,Borroni, Edilio,Bourdeaux, Patrick,Brom, Virginie,Burner, Serge,Fischer, Holger,Hainzl, Dominik,Halm, Remy,Hauser, Nicole,Jolidon, Synese,Lengyel, Judith,Marty, Hans-Peter,Meyer, Thierry,Moreau, Jean-Luc,Mory, Roland,Narquizian, Robert,Nettekoven, Mathias,Norcross, Roger D.,Puellmann, Bernd,Schmid, Philipp,Schmitt, Sebastien,Stalder, Henri,Wermuth, Roger,Wettstein, Joseph G.,Zimmerli, Daniel. "Selective GlyT1 inhibitors: Discovery of [4-(3-fluoro-5- trifluoromethylpyridin-2-yl)piperazin-1-yl][5-methanesulfonyl-2-((S)-2,2, 2-trifluoro-1-methylethoxy)phenyl]methanone (RG1678), a promising novel medicine to treat schizophrenia". supporting information; experimental part. p. 4603 - 4614. Retrieved 2010/09/17.