2096989-55-6

Basic information

• Product Name: (1R,2R,3S,5R)-3-(7-((1S,2R)-2-(3,4-difluorophenyl)cyclopropylaMino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyriMidin-3-yl)-5-(2-hydroxyethoxy)cyclopentane-1,2-diol
• Synonyms: (1R,2R,3S,5R)-3-(7-((1S,2R)-2-(3,4-difluorophenyl)cyclopropylaMino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyriMidin-3-yl)-5-(2-hydroxyethoxy)cyclopentane-1,2-diol
• CAS NO: 2096989-55-6
• Molecular Formula: C23H28F2N6O4S
• Molecular Weight: 522.5680264
• EINECS: -0
• Mol File: 2096989-55-6.mol
• Article Data: 71

Chemical Properties

• Boiling Point: 777.6±70.0 °C(Predicted)
• Appearance: /
• Density: 1.67±0.1 g/cm3(Predicted)
• PKA: 13.26±0.70(Predicted)
• CAS DataBase Reference: (1R,2R,3S,5R)-3-(7-((1S,2R)-2-(3,4-difluorophenyl)cyclopropylaMino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyriMidin-3-yl)-5-(2-hydroxyethoxy)cyclopentane-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R,3S,5R)-3-(7-((1S,2R)-2-(3,4-difluorophenyl)cyclopropylaMino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyriMidin-3-yl)-5-(2-hydroxyethoxy)cyclopentane-1,2-diol(2096989-55-6)
• EPA Substance Registry System: (1R,2R,3S,5R)-3-(7-((1S,2R)-2-(3,4-difluorophenyl)cyclopropylaMino)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyriMidin-3-yl)-5-(2-hydroxyethoxy)cyclopentane-1,2-diol(2096989-55-6)

Safety Data

• Hazardous Substances Data: 2096989-55-6(Hazardous Substances Data)

Usage

Uses

ent-Ticagrelor is the enantiomer of Ticagrelor (T437700); the first reversible oral P2Y12 receptor antagonist that provides faster, greater, and more consistent ADP-receptor inhibition than Clopidogrel. Used in the treatment of acute coronary syndromes (ACS).

Upstream product

• 1427523-80-5 tert-butyl (5-amino-6-(((3aS,4R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)amino)-2-(propylthio) pyrimidin-4-yl)((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)carbamate 
• 220347-05-7 AR-C₁₂₄₉₁₀XX 
• 1006614-49-8 (1R,2S)-2-(3,4-difluorophenyl)cyclopropanamine 
• 1444301-62-5 (1S,2S,3R,5S)-3-((6-chloro-5-nitro-2-(propylthio)pyrimidin-4-yl)amino)-5-(2-hydroxyethoxy)cyclopentane-1,2-diol 
• 1445580-43-7 (1S,2S,3R,5S)-3-(7-hydroxy-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-5-(2-hydroxyethoxy)cyclopentane-1,2-diol 
• 1402222-66-5 trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine hydrochloride 

Downstream Products

• 1251765-07-7 (1S,2S,3R,5S)-3-[7-amino-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]-5-(2-hydroxyethoxy)-1,2-cyclopentanediol 

Relevant articles and documents

Conformational analysis of ticagrelor: effect of noncovalent interaction on conformational population

In order to track the source of duplicated peaks in the 1H-NMR spectrum of Ticagrelor, variable-temperature NMR (VT-NMR) experiment was carried out with temperature increasing from 300 to 343?K. The result showed that the phenomenon was brought forth by coexistence of conformational isomers. Subsequently, conformational search was carried out by molecular mechanics (MM) stimulations associating with quantum mechanics (QM) calculations. The results revealed that the isomers resulting in duplicated proton peaks were introduced by the rotation of 2,4-diflurophenyl group on C3’position of cyclopropyl. Finally, noncovalent interaction (NCI) topological analysis of the conformers exhibited that CH-π interactions and H-bonds play important roles in controlling the population of conformers of ticagrelor.

Method for preparing ticagrelor

The present invention discloses a method for preparing ticagrelor. In the method, 4,6-dihalo-5-nitro-2-propylthiopyrimidine (II) as raw materials and a series of reactions of substitution, reduction,ring formation, substitution, deprotection, etc. are conducted to obtain the ticagrelor. The method has cheap and readily available raw materials, simple process conditions, convenient post-processing, high total yield, and is more suitable for industrial production.

Production process of ticagrelor fine product

The present invention discloses a production process of a ticagrelor fine product. The process comprises the steps of adopting 4,6-dichloro-5-amino-2-propylthiopyrimidine (IIa) and a compound (IIb) asstarting raw materials, and carrying out five processes including a substitution process I, a cyclization process, a substitution process II, a hydrolysis process and a refining process to finally obtain the ticagrelor fine product. The method provides a ticagrelor production process, uses cheap and easily available raw materials, has the advantages of low production cost, simple reaction conditions, convenient post-treatment, high yield and high product purity, and is more suitable for industrial production.