1402150-32-6

Basic information

• Product Name: (1S 2S,3R,5S)-3-[(5-amino-6-chloro-2-(propylthio)pyrimidin-4-yl)amino]-5-(2-hydroxyethoxy)cyclopentane-1,2-diol
• Synonyms: (1S 2S,3R,5S)-3-[(5-amino-6-chloro-2-(propylthio)pyrimidin-4-yl)amino]-5-(2-hydroxyethoxy)cyclopentane-1,2-diol
• CAS NO: 1402150-32-6
• Molecular Weight: 378.88
• Mol File: 1402150-32-6.mol

Chemical Properties

• CAS DataBase Reference: (1S 2S,3R,5S)-3-[(5-amino-6-chloro-2-(propylthio)pyrimidin-4-yl)amino]-5-(2-hydroxyethoxy)cyclopentane-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S 2S,3R,5S)-3-[(5-amino-6-chloro-2-(propylthio)pyrimidin-4-yl)amino]-5-(2-hydroxyethoxy)cyclopentane-1,2-diol(1402150-32-6)
• EPA Substance Registry System: (1S 2S,3R,5S)-3-[(5-amino-6-chloro-2-(propylthio)pyrimidin-4-yl)amino]-5-(2-hydroxyethoxy)cyclopentane-1,2-diol(1402150-32-6)

Safety Data

• Hazardous Substances Data: 1402150-32-6(Hazardous Substances Data)

Usage

Uses

(1S,2S,3R,5S)-3-(5-amino-6-chloro-2-(propylthio)pyrimidin-4-ylamino)-5-(2-hydroxyethoxy)cyclopentane-1,2-diol is an impurity of Ticagrelor (T437700) which is an anticoagulant used in the treatment of acute coronary syndromes.

Upstream product

• 50600-40-3 (3aS,4S,6aR)-4-(iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 
• 4137-56-8 ((3aR,4R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl 4-methylbenzenesulfonate 
• 81026-76-8 ((3aR,4R,6aR)-6-methoxy-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl methanesulfonate 
• 78341-96-5 (3aS,4S,6aR)-4-(bromomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 
• 155934-55-7 (4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde 
• 345898-95-5 N-(((4S,5R)-2,2-dimethyl-5-vinyl-1 ,3-dioxolan-4-yl)methylene)-1-phenylmethanamine oxide 
• 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 
• 155855-53-1 (3aR,4S,6R,6aS)-6-(benzylamino)-2,2-dimethyltetrahydro-3ah-cyclopenta-[d][1,3]-dioxol-4-ol 
• 946855-77-2 4,6-dichloro-5-[(E)-2-(4-phenyl)diazenyl]-2-(propylsulfanyl)pyrimidine 
• 145783-12-6 4,6-dihydroxy-2-(propylsulfanyl)pyrimidine 
• 376608-65-0 2-[[(3aR,4S,6R,6aS)-6-aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol (2R,3R)-2,3-dihydroxybutanedioic acid 
• 1265919-25-2 2-[((3aR,4S,6R,6aS)-6-{[5-nitro-6-chloro-2-(propylthio)-4-pyrimidinyl]amino}-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy]-1-ethanol 
• 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 
• 145783-15-9 4,6-dichloro-2-(propylsulfanyl)-5-pyrimidinamine 

Downstream Products

• 1354945-69-9 9-[(1’R,2’S,3’S,4’S)-2’,3’-dihydroxyl-4'-hydroxyethoxycyclopenta-1'-yl]-9H-2-thiopropyl-6-chloro-8-azepine 
• 274693-27-5 ticagrelor 

Relevant articles and documents

A [...] preparation method and intermediate

The present invention relates to a preparation method and an intermediate of ticagrelor. The preparation method comprises that a compound represented by a formula VIII and a compound represented by a formula VII or a salt thereof as raw materials to carry out a reaction, and the obtained intermediate is subjected to acetonylidene protection group removing, optionally substituted azobenzene protection group removing, and cyclization, and then reacts with a compound represented by a formula II or a salt thereof to prepare the ticagrelor. The preparation method of the present invention has characteristics of short step, high total yield, mild reaction conditions and simple post-treatment, and is suitable for industrial production.

A method for preparing for standard auspicious Luo river

The invention provides a preparation method for ticagrelor. The method comprises the reaction steps shown in the specification, and concretely comprises the following steps: (1) in the presence of an alkali, coupling a formula II compound with a formula III compound to generate a formula IV compound; (2) under an acidic condition, performing reduction and deprotection on the formula IV compound, so as to obtain a formula V compound; (3) performing diazotization and ring closure on the formula V compound, so as to generate a formula VI compound; and (4) under an alkali condition, coupling the formula VI compound with a formula VII compound, so as to obtain ticagrelor shown as a formula I. The method is mild in reaction conditions and simple in post-treatment, is capable of effectively controlling impurities and improving the optical purity of the product, is suitable for industrialized production and has relatively large application value.

INTERMEDIATE OF TICAGRELOR AND PREPARATION METHOD THEREFOR, AND PREPARATION METHOD FOR TICAGRELOR

Disclosed are intermediates of Ticagrelor and a preparation method therefor, and a preparation method for Ticagrelor. Specifically, disclosed is an intermediate, namely, a compound of Formula (VI), for preparing Ticagrelor. Further disclosed is a method for preparing the intermediate and a method for preparing Ticagrelor by using the intermediate. Ticagrelor is prepared by using the intermediate, so that the synthesis process is simple, and a defect that long reaction times under high temperature that are required in the existing methods are avoided. The method is suitable for mass production in industry, energy consumption is reduced, pollution of the environment is reduced, and discharge of waste is reduced.

A PROCESS FOR PREPARATION OF TICAGRELOR AND INTERMEDIATES THEREOF

An improved process for the preparation of ticagrelor and its intermediates thereof; wherein the said process substantially eliminates the potential impurities.

METHOD FOR THE PREPARATION OF TICAGRELOR AND INTERMEDIATES SUITABLE THEREFORE

A method for the preparation of ticagrelor of formula I, wherein the key reaction of the entire synthesis is condensation of an amino cyclopentane diol with pyrimidine, providing the isolated intermediate of formula IV. The amino cyclopentane diol is used for the reaction with pyrimidine without any protecting group on the hydroxyls in positions 1 and 2. Using the compound without a protecting group eliminates the necessity of deprotection in the subsequent synthetic steps.

SYNTHESIS OF TRIAZOLOPYRIMIDINE COMPOUNDS

The present invention relates to the field of organic synthesis and describes the synthesis of specific intermediates suitable for the preparation of triazolopyrimidine compounds such as ticagrelor.

Synthesis of triazolopyrimidine compounds

The present invention relates to the field of organic synthesis and describes the synthesis of specific intermediates suitable for the preparation of triazolopyrimidine compounds such as ticagrelor.

NEW INTERMEDIATES AND PROCESSES FOR PREPARING TICAGRELOR

The present invention is related to new intermediates and processes for preparing Ticagrelor disclosed in this patent application.