249648-16-6

Basic information

• Product Name: [1,2,4]Triazolo[1,5-a]pyrimidin-7-amine, 5-chloro-N-[(1S)-2,2,2-trifluoro-1-methylethyl]-6-(2,4,6-trifluorophenyl)-
• Synonyms: 5-chloro-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl-(S)-(2,2,2-trifluoro-1-methylethyl)amine;5-chloro-N-[(1S)-2,2,2-trifluoro-1-methylethyl]-6-(2,4,6-trifluoro-phenyl)[1,2,4]triazolo[1,5-a]pyrimidine-7-amine;[5-chloro-6-(2,4,6-trifluoro-phenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]-((1S)-2,2,2-trifluoro-1-methyl-ethyl)-amine;5-chloro-6-(2,4,6-trifluorophenyl)-N-[(1S)-2,2,2-trifluoro-1-methylethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine;5-chloro-6-(2,4,6-trifluorophenyl)-7-(1,1,1-trifluoroprop-2-ylamino)-[1,2,4]triazolo[1,5-a]pyrimidine;(S)-5-chloro-6-(2,4,6-trifluorophenyl)-N-(1,1,1-trifluoropropan-2-yl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
• CAS NO: 249648-16-6
• Molecular Formula: C14H8ClF6N5
• Molecular Weight: 395.694
• Mol File: 249648-16-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: 124-126 °C
• Density: 1.69±0.1 g/cm3(Predicted)
• CAS DataBase Reference: [1,2,4]Triazolo[1,5-a]pyrimidin-7-amine, 5-chloro-N-[(1S)-2,2,2-trifluoro-1-methylethyl]-6-(2,4,6-trifluorophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: [1,2,4]Triazolo[1,5-a]pyrimidin-7-amine, 5-chloro-N-[(1S)-2,2,2-trifluoro-1-methylethyl]-6-(2,4,6-trifluorophenyl)-(249648-16-6)
• EPA Substance Registry System: [1,2,4]Triazolo[1,5-a]pyrimidin-7-amine, 5-chloro-N-[(1S)-2,2,2-trifluoro-1-methylethyl]-6-(2,4,6-trifluorophenyl)-(249648-16-6)

Safety Data

• Hazardous Substances Data: 249648-16-6(Hazardous Substances Data)

Upstream product

• 125353-44-8 (S)-2,2,2-trifluoro-1-(methyl)ethylamine hydrochloride 
• 214707-02-5 5,7-dichloro-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine 
• 2367-76-2 2,4,6-trifluorobromobenzene 
• 262609-07-4 diethyl (2,4,6-trifluoro-phenyl)-malonate 
• 125278-10-6 (S)-1,1,1-trifluoropropan-2-amine 

Downstream Products

• 1584642-07-8 (S)-5-chloro-6-(2,6-difluoro-4-(3-((2,2,2-trifluoroethyl)amino)propoxy)phenyl)-N-(1,1,1-trifluoropropan-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine 
• 1584642-02-3 (S)-5-chloro-6-(2,6-difluoro-4-(3-fluoropropoxy)phenyl)-N-(1,1,1-trifluoropropan-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine 
• 1584642-03-4 (S)-5-chloro-6-(4-(3-chloropropoxy)-2,6-difluorophenyl)-N-(1,1,1-trifluoropropan-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine 
• 1584642-04-5 (S)-N-(3-(4-(5-chloro-7-((1,1,1-trifluoropropan-2-yl)amino)-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)-3,5-difluorophenoxy)propyl)acetamide 
• 1584642-05-6 (S)-N-(3-(4-(5-chloro-7-((1,1,1-trifluoropropan-2-yl)amino)-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)-3,5-difluorophenoxy)propyl)pivalamide 
• 943515-67-1 (S)-N-(3-(4-(5-chloro-7-((1,1,1-trifluoropropan-2-yl)amino)-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)-3,5-difluorophenoxy)propyl)-N-methylacetamide 
• 1619924-31-0 (S)-5-azido-6-(2,4,6-trifluorophenyl)-N-(1,1,1-trifluoropropan-2-yl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine 
• 1619924-38-7 C₂₄H₂₁ClF₅N₅O₄S 
• 1584642-06-7 (S)-5-chloro-6-(2,6-difluoro-4-(3-(phenylamino)propoxy)phenyl)-N-(1,1,1-trifluoropropan-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine 
• 849550-05-6 5-chloro-6-{2,6-difluoro-4-[3-(methylamino)propoxy]phenyl}-N-[(1S)-2,2,2-trifluoro-1-methylethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine 
• 879325-04-9 C₁₅H₁₀ClF₆N₅ 

Relevant articles and documents

Evaluation of the Structure-Activity Relationship of Microtubule-Targeting 1,2,4-Triazolo[1,5- a]pyrimidines Identifies New Candidates for Neurodegenerative Tauopathies

Studies in tau and Aβ plaque transgenic mouse models demonstrated that brain-penetrant microtubule (MT)-stabilizing compounds, including the 1,2,4-triazolo[1,5-a]pyrimidines, hold promise as candidate treatments for Alzheimer's disease and related neurodegenerative tauopathies. Triazolopyrimidines have already been investigated as anticancer agents; however, the antimitotic activity of these compounds does not always correlate with stabilization of MTs in cells. Indeed, previous studies from our laboratories identified a critical role for the fragment linked at C6 in determining whether triazolopyrimidines promote MT stabilization or, conversely, disrupt MT integrity in cells. To further elucidate the structure-activity relationship (SAR) and to identify potentially improved MT-stabilizing candidates for neurodegenerative disease, a comprehensive set of 68 triazolopyrimidine congeners bearing structural modifications at C6 and/or C7 was designed, synthesized, and evaluated. These studies expand upon prior understanding of triazolopyrimidine SAR and enabled the identification of novel analogues that, relative to the existing lead, exhibit improved physicochemical properties, MT-stabilizing activity, and pharmacokinetics.

HETEROCYCLIC COMPOUNDS AND THEIR USE FOR THE TREATMENT OF NEURODEGENERATIVE TAUOPATHIES

The present invention is directed to triazolopyrimidine, phenylpyrimidine, pyridopyridazine, and pyridotriazine compounds and their use in the treatment of neurodegenerative disorders.

Process for the preparation of tubulin inhibitors

The present invention provides a process for the preparation of 6-[(substituted)phenyl]-triazolopyrimidine dicarboxylic acid salt and as a hydrated salt having the structural formula (I) wherein: R1 is CF3 or C2F5/su