845614-11-1

Basic information

• Product Name: [4-(3-Fluoro-5-trifluoromethylpyridin-2-yl)piperazin-1-yl][5-Methylsulfonyl-2-[((S)-2,2,2-trifluoro-1-methylethyl)oxy]phenyl]methanone
• Synonyms: (S)-[4-(3-Fluoro-5-trifluoromethylpyridin-2-yl)piperazin-1-yl][5-(methanesulfonyl)-2-(2,2,2-trifluoro-1-methylethoxy)phenyl]methanone;[4-(3-Fluoro-5-trifluoromethylpyridin-2-yl)piperazin-1-yl][5-Methylsulfonyl-2-[((S)-2,2,2-trifluoro-1-methylethyl)oxy]phenyl]methanone;Paliflutine;RG1678;Bitopertin;RO4917838;Palufidine,RG-1678;RG1679
• CAS NO: 845614-11-1
• Molecular Formula: C₂₁H₂₀F₇N₃O₄S
• Molecular Weight: 543
• Product Categories: Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 845614-11-1.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Density: 1.444
• Solubility: insoluble in H2O; ≥17.94 mg/mL in EtOH; ≥88.9 mg/mL in DMSO with ultrasonic
• CAS DataBase Reference: [4-(3-Fluoro-5-trifluoromethylpyridin-2-yl)piperazin-1-yl][5-Methylsulfonyl-2-[((S)-2,2,2-trifluoro-1-methylethyl)oxy]phenyl]methanone(CAS DataBase Reference)
• NIST Chemistry Reference: [4-(3-Fluoro-5-trifluoromethylpyridin-2-yl)piperazin-1-yl][5-Methylsulfonyl-2-[((S)-2,2,2-trifluoro-1-methylethyl)oxy]phenyl]methanone(845614-11-1)
• EPA Substance Registry System: [4-(3-Fluoro-5-trifluoromethylpyridin-2-yl)piperazin-1-yl][5-Methylsulfonyl-2-[((S)-2,2,2-trifluoro-1-methylethyl)oxy]phenyl]methanone(845614-11-1)

Safety Data

• Hazardous Substances Data: 845614-11-1(Hazardous Substances Data)

Usage

Uses

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

Upstream product

• 845616-81-1 1-(3-fluoro-5-(trifluoromethyl)pyridin-2-yl)piperazine 
• 845616-82-2 5-methane-sulfonyl-2-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-benzoic acid 
• 69045-84-7 2,3-dichloro-5-trifluoromethylpyridine 
• 89402-42-6 2,3-difluoro-5-(trifluoromethyl)pyridine 
• 37098-75-2 2-fluoro-5-chlorosulfonylbenzoic acid 
• 445-29-4 o-fluoro-benzoic acid 
• 247569-56-8 2-fluoro-5-(methylsulfonyl)benzoic acid 
• 865663-98-5 2-fluoro-5-methanesulfonylbenzoic acid methyl ester 

Relevant articles and documents

Bitopertin synthetic method and intermediate

The present invention discloses a new synthesis method and intermediates of Bitopertin. According to the Bitopertin synthesis method, 5-methylsulfonyl-2-[(1S)-2,2,2-trifluoro-1-methylethoxy]benzoic acid is adopted as a raw material, and continuous multi-step operations such as chlorination, acylation, deprotection, condensation and re-crystallization are subjected to performed to obtain the Bitopertin, wherein the intermediates in each step do not require further purification, and the total yield can achieve more than or equal to 80%.

SYNTHESIS OF GLYT-1 INHIBITORS

The present invention relates to a process for preparation of a compound of formula I wherein Het, R1, R2, R3, and n are as defined herein and pharmaceutically acceptable acid addition salts thereof, which comprises reacting a compound of formula 21 with a compound of formula 8 to obtain a compound of formula 11 and coupling the compound of formula 11 in the presence of a coupling reagent or the corresponding acid halogenide with a compound of formula 15 to obtain a compound of formula I.