1360549-37-6

Basic information

• Product Name: 5-(4-{(R)-1-cyclopropyl-1-[5-(1H-pyrazol-4-yl)-[1,2,4]oxadiazol-3-yl]ethyl}phenyl)pyrimidin-2-ylamine
• Synonyms: 5-(4-{(R)-1-cyclopropyl-1-[5-(1H-pyrazol-4-yl)-[1,2,4]oxadiazol-3-yl]ethyl}phenyl)pyrimidin-2-ylamine
• CAS NO: 1360549-37-6
• Molecular Weight: 373.417
• Mol File: 1360549-37-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 5-(4-{(R)-1-cyclopropyl-1-[5-(1H-pyrazol-4-yl)-[1,2,4]oxadiazol-3-yl]ethyl}phenyl)pyrimidin-2-ylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-{(R)-1-cyclopropyl-1-[5-(1H-pyrazol-4-yl)-[1,2,4]oxadiazol-3-yl]ethyl}phenyl)pyrimidin-2-ylamine(1360549-37-6)
• EPA Substance Registry System: 5-(4-{(R)-1-cyclopropyl-1-[5-(1H-pyrazol-4-yl)-[1,2,4]oxadiazol-3-yl]ethyl}phenyl)pyrimidin-2-ylamine(1360549-37-6)

Safety Data

• Hazardous Substances Data: 1360549-37-6(Hazardous Substances Data)

Upstream product

• 1401466-58-7 dicyclohexylammonium 2-(4-bromophenyl)-2-cyclopropylpropanoate 
• 765-43-5 Cyclopropyl methyl ketone 
• 106-37-6 1.4-dibromobenzene 
• 37718-11-9 1H-pyrazole-4-carboxylic acid 
• 1448893-30-8 (R)-2-(4-bromophenyl)-2-cyclopropylpropanal 
• 5391-88-8 (S)-1-(4-bromophenyl)ethanol 
• 99-90-1 para-bromoacetophenone 
• 1360551-95-6 (R)-2-(4-bromophenyl)-2-cyclopropyl-N′-hydroxypropanimidamide 
• 1448893-31-9 (R)-2-(4-bromophenyl)-2-cyclopropylpropanal oxime 
• 1360552-08-4 (R)-2-[4-(2-aminopyrimidin-5-yl)phenyl]-2-cyclopropylpropionitrile 
• 1360551-90-1 (R)-2-(4-bromo-phenyl)-2-cyclopropylpropionitrile 
• 1360551-88-7 2-(4-bromo-phenyl)-2-cyclopropylpropionitrile 
• 56041-75-9 1-(4-bromophenyl)-1-cyclopropylethan-1-ol 
• 1360552-09-5 (R,Z)-2-(4-(2-aminopyrimidin-5-yl)phenyl)-2-cyclopropyl-N′-hydroxypropanimidamide 

Downstream Products

• 1360552-61-9 2-{2-[4-(3-{(R)-1-[4-(2-amino-pyrimidin-5-yl)-phenyl]-1-cyclopropyl-ethyl}-[1,2,4]oxadiazol-5-yl)-pyrazol-1-yl]-ethyl}-isoindole-1,3-dione 
• 1360550-04-4 2-[4-(3-{(1R)-1-[4-(2-aminopyrimidin-5-yl)phenyl]-1-cyclopropylethyl}-1,2,4-oxadiazol-5-yl)-1H-pyrazol-1-yl]-N,N-dimethylacetamide 
• 1360550-70-4 5-[4-((R)-1-cyclopropyl-1-{5-[1-(2-dimethylaminoethyl)-1H-pyrazol-4-yl]-[1,2,4]oxadiazol-3-yl}-ethyl)phenyl]pyrimidin-2-ylamine 
• 1360550-78-2 5-[4-((R)-1-{5-[1-(2-aminoethyl)-1H-pyrazol-4-yl]-[1,2,4]oxadiazol-3-yl}-1-cyclopropylethyl)phenyl]pyrimidin-2-ylamine 

Relevant articles and documents

Early Development Scale-Up of a Structurally-Challenging 5-Lipoxygenase Activating Protein (FLAP) Inhibitor

A practical and efficient synthesis of the FLAP inhibitor 1 was developed addressing multiple scale-up and safety concerns posed by the established synthesis and utilized a resolution strategy (replacing supercritical fluid chromatography (SFC) separation) for expedient access to the key structural component of 1: the challenging chiral quaternary center. Also highlighted are in situ IR monitoring, condensation to form the 1,2,4-oxadiazole ring, and an efficient Suzuki-Miyaura coupling.

Development of an asymmetric synthesis of a chiral quaternary FLAP inhibitor

A practical sequence involving a noncryogenic stereospecific boronate rearrangement followed by a robust formylation with an in situ generated DCM anion has been developed for the asymmetric construction of an all-carbon quaternary stereogenic center of a FLAP inhibitor. The key boronate rearrangement was rendered noncryogenic and robust by using LDA as the base and instituting an in situ trapping of the unstable lithiated benzylic carbamate with the boronic ester. A similar strategy was implemented for the DCM formylation reaction. It was found that the 1,2-boronate rearrangement for the formylation reaction could be temperature-controlled, thus preventing overaddition of the DCM anion and rendering the process reproducible. The robust stereospecific boronate rearrangement and formylation were utilized for the practical asymmetric synthesis of a chiral quaternary FLAP inhibitor.

OXADIAZOLE INHIBITORS OF LEUKOTRIENE PRODUCTION

The present invention relates to compound of formula (I): or pharmaceutically acceptable salts thereof, wherein R1-R5 are as defined herein. The invention also relates to pharmaceutical compositions comprising these compounds, methods of using these compounds in the treatment of various diseases and disorders, processes for preparing these compounds and intermediates useful in these processes.