(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]tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol

Manufacturer: Hangzhou Royalchem Co.,LTD.

Website:   www.cnroyalchem.com

【 Providing a complete set of intermediates and impurities for Ticagrelor 】

【 Providing a complete set of intermediates and impurities for Ticagrelor 】

【 Providing a complete set of intermediates and impurities for Ticagrelor 】

Here is a detailed product description for the compound specified by the CAS number  274693-49-1  and the systematic name  (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]tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol :

Product Identification

Chemical Name:   (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]tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol

CAS Registry Number:  274693-49-1

Synonyms:  Commonly abbreviated based on its structure or project code (specific synonyms would depend on the research context). Examples might include references to the core triazolopyrimidine scaffold and the cyclopropylamino-difluorophenyl moiety.

Molecular Formula:  C₂₅H₂₈F₂N₆O₃S

Molecular Weight:  506.60 g/mol (calculated exact mass)

Structural Characteristics

Core Scaffold:  Contains a  1,2,3-triazolo[4,5-d]pyrimidine  core, which is a fused heterocyclic system known for its biological activity in various therapeutic areas.

Key Substituents:

7-Position:  A secondary amine linkage to a  [(1R,2S)-2-(3,4-difluorophenyl)cyclopropyl]  group. This moiety features a chiral cyclopropane ring directly attached to a 3,4-difluorinated benzene ring, contributing lipophilicity and potential target interaction points.

5-Position:  A  propylthio (-S-CH₂-CH₂-CH₃)  group, providing lipophilic character and potential metabolic sites.

3-Position:  Substituted with the  tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-ol  group. This is a  protected diol system , specifically a chiral cyclopentane ring fused to a 2,2-dimethyl-1,3-dioxolane (acetone ketal) protecting group, with a free hydroxyl group remaining at the 4-position. This indicates the parent compound likely contains a diol (e.g., a cyclopentane diol or a ribose-like sugar derivative) where one diol is protected as an acetonide.

Stereochemistry:  The compound possesses  multiple defined chiral centers  specified as:

(3aR,4S,6R,6aS)  for the cyclopentanedioxol moiety.

(1R,2S)  for the cyclopropyl group attached to the difluorophenyl ring. This specific stereochemistry is crucial for its biological activity and physicochemical properties.

Physical and Chemical Properties (Estimated/Speculative - Requires Experimental Confirmation)

Appearance:  Typically expected to be a solid (powder or crystals). Color could range from white to off-white or tan.

Solubility:

Likely  moderately soluble  in organic solvents like DMSO, DMF, methanol, ethanol, acetonitrile, dichloromethane.

Likely  low solubility  in water due to significant lipophilic components (cyclopropylphenyl, propylthio, ketal protection).

Stability:

Light/Temperature:  Should be stored protected from light and moisture. Stability at room temperature may vary; long-term storage often recommended at -20°C.

Hydrolysis:  The  dioxolane (ketal) protecting group  is stable to base but can be susceptible to hydrolysis under acidic conditions. Stability in solution (e.g., DMSO) should be monitored.

Oxidation:  The  thioether (propylthio)  group could potentially be oxidized to sulfoxide or sulfone over time or under oxidizing conditions.

Applications and Usage

Research Use Only (RUO):  This compound is  exclusively intended for research and development purposes .

Primary Context:  Based on its complex structure and defined stereochemistry, it is highly likely to be a  pharmaceutical intermediate , a  key building block , or a  biological probe  in medicinal chemistry programs.

Potential Therapeutic Targets:  The triazolopyrimidine scaffold coupled with the cyclopropylamino-difluorophenyl motif strongly suggests potential activity as a  kinase inhibitor  (e.g., targeting kinases like ALK, FLT3, JAK, etc.) or possibly as a modulator of other enzymatic targets. The protected diol moiety suggests potential development into a  nucleoside/tide analogue  therapeutic.

Role in Synthesis:  Likely serves as a critical chiral intermediate in the multi-step synthesis of a more complex active pharmaceutical ingredient (API), where the ketal protection needs eventual removal.

Handling and Safety

Precautionary Statements:  Standard laboratory precautions should be followed.

P264:  Wash hands thoroughly after handling.

P280:  Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338:  IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

P337+P313:  If eye irritation persists: Get medical advice/attention.

P501:  Dispose of contents/container in accordance with local/regional/national/international regulations.

Hazard Statements:  A complete safety assessment requires experimental data (SDS). Based on structure:

H315:  Causes skin irritation.

H319:  Causes serious eye irritation.

H335:  May cause respiratory irritation.

(Speculative):  Potential hazards associated with dust inhalation or specific organ toxicity would depend on biological profiling.

Storage:  Store in a cool (-20°C recommended), dry place, protected from light, under inert atmosphere (e.g., N₂ or Ar) if sensitive to oxidation. Keep container tightly sealed.