(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarbonyl azide

Base Information

• Chemical Name: (1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarbonyl azide
• CAS No.: 378236-67-0
• Molecular Formula: C₁₀H₇F₂N₃O
• Molecular Weight: 223.182
• Mol file: 378236-67-0.mol

Synonyms:(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarbonyl azide

Chemical Property of (1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarbonyl azide

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

(1R,2R)-2-(3,4-Difluorophenyl)-cyclopropanecarbonylAzide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (1R,2R)-2-(3,4-Difluorophenyl)-cyclopropanecarbonyl Azide is a useful synthetic intermediate in the synthesis of Ticagrelor (T437700); the first reversible oral P2Y12 receptor antagonist that provides faster, greater, and more consistent ADP-receptor inhibition than Clopidogrel. Ticagrelor is also used in the treatment of acute coronary syndromes (ACS).

Technology Process of (1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarbonyl azide

There total 6 articles about (1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarbonyl azide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 74.0%

(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarbohydrazide (1459720-05-8) → (1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarbonyl azide (378236-67-0)

Guidance literature:

With acetic acid; sodium nitrite; at 25 ℃; for 0.5h;

Reference yield:

1,3-dioxoisoindolin-2-yl (1R,2R)-2-(3,4-difluorophenyl)cyclopropane-1-carboxylate → (1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarbonyl azide (378236-67-0)

Guidance literature:

With hydrogenchloride; sodium azide; In water; acetone; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1002/anie.201814123

Reference yield:

trans-(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylic acid (220352-36-3,1006614-50-1) + chloroformic acid ethyl ester (541-41-3) → (1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarbonyl azide (378236-67-0)

Guidance literature:

trans-(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylic acid; chloroformic acid ethyl ester; With TEA; In acetone;

With sodium azide; In water; Further stages.;

DOI:10.1016/j.bmcl.2007.07.057

upstream raw materials:

trans-(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarboxylic acid

chloroformic acid ethyl ester

(1R,2R)-2-(3,4-difluorophenyl)cyclopropanecarbohydrazide

(1R,2S)-2-(3,4-difluorophenyl)cyclopropanoic acid methyl ester

Downstream raw materials:

tert-butyl ((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)carbamate

trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine hydrochloride

(1R,2S)-2-(3,4-difluorophenyl)cyclopropanamine

benzyl ((1R,2S)-2-(3,4-difluorophenyl)cyclopropyl)carbamate

Refernces

• 1、 -. "SYNTHESIS OF 2-(3,4-DIFLUOROPHENYL)CYCLOPROPANAMINE DERIVATIVES AND SALTS". Page/Page column 21. . Retrieved 2013/10/21.
• 2、 Springthorpe, Brian,Bailey, Andrew,Barton, Patrick,Birkinshaw, Timothy N.,Bonnert, Roger V.,Brown, Roger C.,Chapman, David,Dixon, John,Guile, Simon D.,Humphries, Robert G.,Hunt, Simon F.,Ince, Francis,Ingall, Anthony H.,Kirk, Ian P.,Leeson, Paul D.,Leff, Paul,Lewis, Richard J.,Martin, Barrie P.,McGinnity, Dermot F.,Mortimore, Michael P.,Paine, Stuart W.,Pairaudeau, Garry,Patel, Anil,Rigby, Aaron J.,Riley, Robert J.,Teobald, Barry J.,Tomlinson, Wendy,Webborn, Peter J.H.,Willis, Paul A.. "From ATP to AZD6140: The discovery of an orally active reversible P2Y12 receptor antagonist for the prevention of thrombosis". . p. 6013 - 6018. Retrieved 2008/04/02.