378236-67-0

Basic information

• Product Name: (1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarbonyl azide
• Synonyms: (1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarbonyl azide
• CAS NO: 378236-67-0
• Molecular Weight: 223.182
• Mol File: 378236-67-0.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarbonyl azide(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarbonyl azide(378236-67-0)
• EPA Substance Registry System: (1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarbonyl azide(378236-67-0)

Safety Data

• Hazardous Substances Data: 378236-67-0(Hazardous Substances Data)

Usage

Description

(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarbonyl azide is a chiral compound characterized by its specific stereochemistry, with the R configuration at both the first and second carbon atoms. It features a cyclopropane ring fused to a carbonyl group, which is further substituted with an azide group and a 3,4-difluorophenyl moiety. This molecule is known for its reactivity and utility in the synthesis of various pharmaceutical compounds.

Uses

Used in Pharmaceutical Industry:
(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarbonyl azide is used as a synthetic intermediate for the production of Ticagrelor (T437700), which is the first reversible oral P2Y12 receptor antagonist. Ticagrelor provides faster, greater, and more consistent ADP-receptor inhibition compared to Clopidogrel, making it a valuable alternative in the treatment of acute coronary syndromes (ACS). (1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarbonyl azide's unique structure and reactivity enable the development of new therapeutic agents with improved efficacy and safety profiles.

Upstream product

• 1459720-05-8 (1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarbohydrazide 
• 1459720-02-5 (1R,2S)-2-(3,4-difluorophenyl)cyclopropanoic acid methyl ester 
• 220352-36-3 trans-(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylic acid 
• 541-41-3 chloroformic acid ethyl ester 

Downstream Products

• 1350749-64-2 tert-butyl ((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)carbamate 
• 1402222-66-5 trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine hydrochloride 
• 1006614-49-8 (1R,2S)-2-(3,4-difluorophenyl)cyclopropanamine 
• 1427523-91-8 benzyl ((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)carbamate 

Relevant articles and documents

General Cyclopropane Assembly by Enantioselective Transfer of a Redox-Active Carbene to Aliphatic Olefins

Asymmetric cyclopropane synthesis currently requires bespoke strategies, methods, substrates, and reagents, even when targeting similar compounds. This approach slows down discovery and limits available chemical space. Introduced herein is a practical and versatile diazocompound and its performance in the first unified asymmetric synthesis of functionalized cyclopropanes. The redox-active leaving group in this reagent enhances the reactivity and selectivity of geminal carbene transfer. This effect allowed the asymmetric cyclopropanation of various olefins, including unfunctionalized aliphatic alkenes, that enables the three-step total synthesis of (?)-dictyopterene A. This unified synthetic approach delivers high enantioselectivities that are independent of the stereoelectronic properties of the functional groups transferred. Our results demonstrate that orthogonally differentiated diazocompounds are viable and advantageous equivalents of single-carbon chirons.

SYNTHESIS OF 2-(3,4-DIFLUOROPHENYL)CYCLOPROPANAMINE DERIVATIVES AND SALTS

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.

Novel triazolo pyrimidine compounds

The present invention relates to a pyrimidine compound (I) useful as a pharmaceutical intermediate, to a process for preparing said pyrimidine compound, to intermediates used in said process, and to the use of said pyrimidine compound in the preparation of pharmaceuticals.