220347-05-7

Basic information

• Product Name: AR-C 124910XX
• Synonyms: AR-C 124910XX;Deshydroxyethoxy Ticagrelor;(1S,2R,3S,4R)-4-(7-(((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)cyclopentane-1,2,3-triol;Ticagrelor impurity G (Ticagrelor metabolite)
• CAS NO: 220347-05-7
• Molecular Formula: C₂₁H₂₄F₂N₆O₃S
• Molecular Weight: 478.5154664
• Product Categories: Aromatics, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 220347-05-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 722.7±70.0 °C(Predicted)
• Appearance: /
• Density: 1.75±0.1 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 13.38±0.70(Predicted)
• CAS DataBase Reference: AR-C 124910XX(CAS DataBase Reference)
• NIST Chemistry Reference: AR-C 124910XX(220347-05-7)
• EPA Substance Registry System: AR-C 124910XX(220347-05-7)

Safety Data

• Hazardous Substances Data: 220347-05-7(Hazardous Substances Data)

Usage

Uses

Deshydroxyethoxy Ticagrelor analog of Ticagrelor (T437700) an antiplatelet agent, and preventative in the treatment of heart attacks, myocardial infarction, and other pulmonary diseases.

Upstream product

• 274693-27-5 ticagrelor 
• 532-20-7 D-Ribose 
• 1006376-62-0 (1R,2R)-trans-2(3,4-difluorophenyl)cyclopropyl carboxamide 
• 376608-70-7 trans-(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarbonyl chloride 
• 1006376-63-1 (S)-2-(3,4-difluorophenyl)ethylene oxide 
• 1006376-60-8 (1S)-2-chloro-1-(3,4-difluorophenyl)-1-ethanol 
• 376608-73-0 4,6-dichloro-5-((E)-2-(4-methylphenyl)diazenyl)-2-(propylsulfanyl)pyrimidine 
• 50600-40-3 (3aS,4S,6aR)-4-(iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 
• 155855-51-9 tetrahydro-2,2-dimethyl-6-phenylmethyl-(3aS,4S,7R,7aS)-4,7-methano-4H-1,3-dioxolo[4,5-d][1,2]oxazine 
• 155899-66-4 (3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol 
• 367-11-3 ortho-difluorobenzene 
• 145783-12-6 4,6-dihydroxy-2-(propylsulfanyl)pyrimidine 
• 274693-49-1 (3aR,4S,6R,6aS)-6-(7-(((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol 
• 220241-61-2 (3aR,4S,6R,6aS)-6-(7-chloro-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol 

Downstream Products

• 274693-49-1 (3aR,4S,6R,6aS)-6-(7-(((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)amino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol 
• 274693-27-5 ticagrelor 

Relevant articles and documents

Concise synthesis of the major metabolite M8 from ticagrelor and simultaneous determination of ticagrelor and M8 by a novel LC/MS method

Ticagrelor is an oral antiplatelet agent that has been approved for preventing de novo and recurrent acute coronary syndrome. To date, only a few studies have attempted to clarify population differences in the pharmacokinetics and pharmacodynamics of ticagrelor between Caucasians and Asians. Our aim was to develop a simple quantification method for ticagrelor and its pharmacologically active metabolite M8 (AR-C124910XX) in human plasma and urine. First, we concisely synthesized M8 from ticagrelor via a five-step sequence: the hydroxyethyl group of ticagrelor was removed by bromination and subsequent zinc-mediated chemoselective reduction. Then, we developed a simple liquid chromatography–mass spectrometry method using ticlopidine as an internal standard. Ticagrelor, M8, and internal standard were separated with a reverse-phase C18 column, and ticagrelor and M8 were detected at m/z [+] of 523.25 and 479.25, respectively, with good sensitivity and precision in the concentration ranges of 10 to 100 μM and 5 to 50 μM, respectively. This novel liquid chromatography–mass spectrometry system may be attractive to investigators in private laboratories because it is less costly than liquid chromatography/mass spectrometry/mass spectrometry systems. Our method is expected to accelerate further clinical studies on the disposition and pharmacodynamics of ticagrelor.

Method of synthesis of Ticagrelor

The invention provides a method of synthesis of Ticagrelor (1). The method comprises the steps that firstly a compound (2) and a compound (3) are subject to a substitution reaction to prepare a compound (4); the compound (4) after being subject to the substitution reaction of sulfur alcohol is prepared into a compound (5); the compound (5) and a compound (6) after being subject to the substitution reaction of palladium catalyst non-symmetric terpene propyl alcohol is prepared into a compound (7); the compound (7) after being subject to non-asymmetric di-hydroxylation reaction is prepared into a compound (8); the compound (8) after being subject to di-hydroxy protective reaction is prepared into a compound (9); the compound (9) after being subject to the substitution reaction of hydroxyl is prepared into a compound (10); finally Ticagrelor (1) is obtained by subjecting the compound (10) to the deprotection reaction of hydroxyl. The method of synthesis of Ticagrelor is simple to operate, low in production cost, high in product quality, and suitable for industrial production. (The picture file is appended to the application.).