1224944-77-7

Basic information

• Product Name: Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate
• Synonyms: Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate;5-chloropyrazolo[1,5-a]pyriMidine-3-carboxylate;5-Chloro-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester
• CAS NO: 1224944-77-7
• Molecular Formula: C₉H₈ClN₃O₂
• Molecular Weight: 225.63172
• Mol File: 1224944-77-7.mol
• Article Data: 21

Chemical Properties

• Appearance: /
• Density: 1.47±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -2.44±0.40(Predicted)
• CAS DataBase Reference: Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate(1224944-77-7)
• EPA Substance Registry System: Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate(1224944-77-7)

Safety Data

• Hazardous Substances Data: 1224944-77-7(Hazardous Substances Data)

Usage

Uses

Ethyl 5-Chloropyrazolo[1,5-a]pyrimidine-3-carboxylate is used in preparation of antitumor pyrazolopyrimidine compound and it intermediates.

Upstream product

• 42466-67-1 ethyl (ethoxymethylene)cyanoacetate 
• 94-05-3 ethyl (ethoxymethylene)cyanoacetate 
• 144918-37-6 (E)-ethyl 2-cyano-3-ethoxyacrylate 
• 926663-00-5 5-hydroxypyrazole[1,5-a]pyrimidine-3-carboxylic acid ethyl ester 
• 6994-25-8 3-amino-4-pyrazolecarboxylic acid ethyl ester 
• 1260243-04-6 ethyl 5-amino-1H-pyrazole-4-carboxylate 

Downstream Products

• 1260845-57-5 ethyl (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate 
• 1260840-74-1 5-((R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)-N-((S)-2,3-dihydroxypropyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide 
• 1260846-60-3 (R)-5-(5-(2,5-difluorophenyl)-2,2-dimethylpyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid 
• 1260842-01-0 5-((R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)-N-((S)-2,3-dihydroxypropoxy)pyrazolo[1,5-a]pyrimidine-3-carboxamide 
• 1260846-92-1 5-((R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)-N-(((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)pyrazolo[1,5-a]pyrimidine-3-carboxamide 
• 1260845-56-4 (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid 
• 1260845-64-4 (R)-5-(2-(5-fluoro-2-methoxyphenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid 
• 1260843-28-4 5-((R)-2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl)-N-((trans)-4-hydroxycyclohexyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide 
• 1260840-05-8 (R)-N-tert-butyl-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide 
• 1260840-10-5 (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)-N-(3-methylpyridin-2-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide 
• 1260846-57-8 (R)-ethyl 5-(5-(2,5-difluorophenyl)-2,2-dimethylpyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate 
• 1260845-87-1 (R)-ethyl 5-(2-(5-fluoro-2-(trifluoromethyl)phenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate 
• 1431654-51-1 5-(2-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid 
• 1431645-12-3 N-(pyridin-4-yl)-5-(2-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide 

Relevant articles and documents

Discovery of a novel series of pyrazolo[1,5-a]pyrimidine-based phosphodiesterase 2A inhibitors structurally different from N-((1S)-1-(3-fluoro-4-(trifluoromethoxy)phenyl)-2-methoxyethyl)-7-methoxy-2-oxo-2,3-dihydropyrido[2,3-b]pyrazine-4(1H)-carboxamide (TAK-915), for the treatment of cognitive disorders

It has been hypothesized that selective inhibition of phosphodiesterase (PDE) 2A could potentially be a novel approach to treat cognitive impairment in neuropsychiatric and neurodegenerative disorders through augmentation of cyclic nucleotide signaling pathways in brain regions associated with learning and memory. Following our earlier work, this article describes a drug design strategy for a new series of lead compounds structurally distinct from our clinical candidate 2 (TAK-915), and subsequent medicinal chemistry efforts to optimize potency, selectivity over other PDE families, and other preclinical properties including in vitro phototoxicity and in vivo rat plasma clearance. These efforts resulted in the discovery of N-((1S)-2-hydroxy-2-methyl-1-(4-(trifluoromethoxy)phenyl)propyl)-6-methyl-5-(3-methyl-1H-1,2,4triazol-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (20), which robustly increased 3′,5′-cyclic guanosine monophosphate (cGMP) levels in the rat brain following an oral dose, and moreover, attenuated MK-801-induced episodic memory deficits in a passive avoidance task in rats. These data provide further support to the potential therapeutic utility of PDE2A inhibitors in enhancing cognitive performance.

A class of FLT3 kinase inhibitors, preparation and application thereof

The invention relates to a class of FLT3 kinase inhibitors, preparation and application thereof, wherein specifically the compound has a structure represented by a formula (I), and all groups and substituents are defined in the specification. The invention also discloses a preparation method of the compound, and application of the compound in inhibition of FLT3.

DEGRADERS THAT TARGET ALK AND THERAPEUTIC USES THEREOF

Disclosed are bispecific compounds (degraders) that target ALK for degradation. Also disclosed are pharmaceutical compositions containing the degraders and methods of using the compounds to treat diseases and disorders characterized or mediated by aberrant ALK activity