220352-36-3

Basic information

• Product Name: (1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylic acid
• Synonyms: (1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylic acid;(1R,2R)-2-(3,4-difluorophenyl)cyclopropane-1-carboxylic acid;Ticagrelor Related Compound 28
• CAS NO: 220352-36-3
• Molecular Formula: C₁₀H₈F₂O₂
• Molecular Weight: 198.1661264
• EINECS: 1533716-785-6
• Mol File: 220352-36-3.mol

Chemical Properties

• Boiling Point: 308.1±42.0 °C(Predicted)
• Appearance: /
• Density: 1.435±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Sparingly)
• PKA: 4.53±0.10(Predicted)
• CAS DataBase Reference: (1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylic acid(220352-36-3)
• EPA Substance Registry System: (1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylic acid(220352-36-3)

Safety Data

• Hazardous Substances Data: 220352-36-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylic acid is used as an intermediate for the preparation of AZD6140, an orally active reversible P2Y12 receptor antagonist. This application is significant for the prevention of thrombosis, a condition characterized by the formation of blood clots within the circulatory system, which can lead to serious health complications such as heart attacks and strokes.
Additionally, (1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylic acid is used in the synthesis of triazolopyrimidine derivatives, which act as P2T receptor antagonists. These derivatives have potential applications in the treatment of various diseases and disorders, highlighting the versatility of this intermediate in the development of novel therapeutic agents.

Upstream product

• 1006376-60-8 (1S)-2-chloro-1-(3,4-difluorophenyl)-1-ethanol 
• 1006376-63-1 (S)-2-(3,4-difluorophenyl)ethylene oxide 
• 367-11-3 ortho-difluorobenzene 
• 51336-95-9 2-chloro-1-(3,4-difluorophenyl)ethan-1-one 
• 1006376-61-9 (1R,2R)-2-(3,4-difluorophenyl)-1-cyclopropanecarboxylic acid ethyl ester 
• 64248-58-4 1,2-difluoro-4-iodo-benzene 
• 1759-53-1 cyclopropanecarboxylic acid 
• 692288-05-4 C₄H₅IO₂ 
• 168267-41-2 (3,4-difluorophenyl)boronic acid 
• 405-03-8 1-(3,4-difluorophenyl)ethene 
• 34036-07-2 3,4 difluorobenzaldehyde 
• 1043546-64-0 3,4-difluorocinnamoyl chloride 
• 112897-97-9 (E)-3-(3,4-difluorophenyl)acrylic acid 
• 1334528-90-3 (E)-3-(3,4-difluorophenyl)acrylaldehyde 

Downstream Products

• 376608-70-7 trans-(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarbonyl chloride 
• 378236-67-0 (1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarbonyl azide 
• 1006614-49-8 (1R,2S)-2-(3,4-difluorophenyl)cyclopropanamine 
• 274693-26-4 [3aR-[3aα,4α,6α,(1R,2S),6aα]]-2-[6-[[[7-(2-(3,4-difluorophenyl)cyclopropyl)]amino-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]tetrahydro-2,2-dimethyl-4H-cyclopenteno-1,3-dioxolan-4-yl]oxy]ethanol 
• 274693-27-5 ticagrelor 
• 1353964-60-9 trans-(1R,2R)-2-(3,4-difluorophenyl)-N-hydroxycyclopropanecarboxamide 
• 1353964-63-2 trans-(1R,2R)-N-(acetyloxy)-2-(3,4-difluorophenyl)cyclopropane carboxamide 
• 1353964-70-1 trans-(1R,2S)-2-(3,4-difluorophenyl)-cyclopropylamine (S)-ketopinate 
• 1353964-72-3 trans-(1R,2S)-2-(3,4-difluorophenyl)-cyclopropylamine (D)-camphorsulfonate 
• 1353964-85-8 trans-(1R,2S)-2-(3,4-difluorophenyl)-cyclopropylamine (R)-(-)-α-methoxyphenyl acetate 
• 220347-05-7 AR-C₁₂₄₉₁₀XX 
• 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 
• 1006376-62-0 (1R,2R)-trans-2(3,4-difluorophenyl)cyclopropyl carboxamide 
• 1459720-02-5 (1R,2S)-2-(3,4-difluorophenyl)cyclopropanoic acid methyl ester 

Relevant articles and documents

Preparation method of phenyl-containing compound

The present invention discloses a method for preparing an phenyl-containing compound. The present invention provides a method for preparing a compound shown in formula I, comprising the following steps: in the presence of formamide or acetamide, in the pr

Preparation method of ticagrelor key intermediate

The invention relates to the technical field of medicines, in particular to a preparation method of a ticagrelor key intermediate, which comprises the following steps: dissolving a compound shown as a formula I and 3,4-difluoroiodobenzene in a solvent, adding a catalyst, a first ligand, a second ligand, acid and a metal salt catalyst, and heating for reaction to obtain a compound shown as a formula II; dissolving the compound shown in the formula II and alkali in a solvent, stirring the mixture for reaction, dropwise adding bromine, continuing the reaction after dropwise adding, and adding sodium thiosulfate to generate a compound shown in a formula III after the reaction is finished. The preparation method of the ticagrelor chiral intermediate is short and novel in route, mild in reaction condition, economical and effective, higher in yield compared with an existing preparation method, and suitable for large-scale industrial production.

Preparation method of ticagrelor key intermediate

The invention belongs to the technical field of medicines, and particularly relates to a preparation method of a ticagrelor key intermediate, and the method is used for preparing the ticagrelor intermediate, has the advantages of short reaction steps, mild reaction conditions and higher yield than the existing preparation method, is economical and effective, and is suitable for large-scale industrial production.

Method for synthesizing (1R,2R)-2-(3,4-difluorophenyl)cyclopropane-carboxylic acid

The invention discloses a method for synthesizing a compound, i.e., (1R,2R)-2-(3,4-difluorophenyl)cyclopropane-carboxylic acid. A synthesis route is shown as follows. The compound represented by a formula I shown in the description is synthesized through

Ticagrelor key intermediate and preparation method thereof

The invention discloses a ticagrelor key intermediate 1-TK-acid and a preparation method of the ticagrelor key intermediate 1-TK-acid. The ticagrelor key intermediate has a structure shown in a formula (D) which is shown in the description. The method comprises the following steps of (1) preparing 2-chloro-1-(3,4-difluorophenyl)ethanone; (2) preparing a methylbenzene solution of 2-chloro-1-S-(3,4-difluorophenyl)ethyl alcohol; (3) preparing the ticagrelor key intermediate 1-TK-acid. The ticagrelor key intermediate 1-TK-acid has the advantages that the technology is matured and stable, the product quality is stable, the production technology is safe and reliable, and the ticagrelor key intermediate 1-TK-acid is suitable for industrialized production.

Preparation method of ticagrelor

The invention discloses a preparation method of ticagrelor. The preparation method comprises the following steps: (1) preparation of ticagrelor intermediate product 1-TK acid; (2) preparation of ticagrelor intermediate product 2-TK-amide; (3) preparation of ticagrelor intermediate product 3-TK-amino compound hydrochloride; (4) preparation of ticagrelor intermediate product 4-TK-amino compound R-tartrate; ( 5) preparation of ticagrelor intermediate product 5-TK-amino compound L-mandelate; and (6) preparation of ticagrelor-TK. The preparation method has the advantages of cost advantage, mature and stable process, stable product quality, and safe and reliable production process.

Ticagrelor intermediate, and preparation method thereof

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for standard auspicious Luo river intermediate preparation method

The inventiondiscloses a preparation method of ticagrelor. The method comprises the following steps: (1) reducing a compound shown in a formula III in the presence of a proton source provided by sodium borohydride or potassium borohydride and diethyl aniline hydrochloride to obtain a compound shown in a formula IV; (2) reacting the compound IV in the presence of alkali to generate a compound VI; (3) hydrolyzing the compound VI without purification to generate a compound VII; (4) reacting the compound VII to generate acyl chloride, reacting the acyl chloride to generate formamide, thus obtaining a compound shown in a formula IX; and (5) carrying out Hofmann rearrangement on the compound IX to obtain a compound shown in a formula II. Regents used in the method are nontoxic, harmless, environmentally friendly and low in price; the used key reagents can be recycled. Therefore, the method is applicable to industrial production.

Comparison of a Batch and Flow Approach for the Lipase-Catalyzed Resolution of a Cyclopropanecarboxylate Ester, A Key Building Block for the Synthesis of Ticagrelor

In this study a batch reactor process is compared to a flow chemistry approach for lipase-catalyzed resolution of the cyclopropanecarboxylate ester (±)-3. (1R,2R)-3 is a precursor of the amine (1R,2S)-2 which is a key building block of the API ticagrelor. For both flow and batch operation, the biocatalyst could be recycled several times, whereas in the case of the flow process the reaction time was significantly reduced.

PREPARATION OF TICAGRELOR

Provided are processes for preparing Ticagrelor and its intermediates that are useful in the processes. Also provided are salts of Ticagrelor, their processes and solid dispersion of Ticagrelor having Ticagrelor in amorphous form.