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

Description

Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate is an organic compound that serves as an intermediate in the synthesis of various pyrazolopyrimidine-based compounds. It is characterized by its unique molecular structure, which features a pyrazolo[1,5-a]pyrimidine core with a chloro substituent at the 5-position and an ester group at the 3-position. ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate is of significant interest in the field of medicinal chemistry due to its potential applications in the development of novel therapeutic agents.

Uses

Used in Pharmaceutical Industry:
Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate is used as a key intermediate in the synthesis of antitumor pyrazolopyrimidine compounds. Its unique chemical structure allows for the development of molecules with potential antiproliferative and cytotoxic properties, making it a valuable component in the creation of new cancer therapies.
In the synthesis of these antitumor agents, ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate can be further modified through various chemical reactions to introduce functional groups and structural motifs that enhance the biological activity and selectivity of the resulting compounds. This allows researchers to explore a wide range of potential therapeutic agents with improved efficacy and reduced side effects compared to existing treatments.
Furthermore, the use of ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate as a starting material in the synthesis of pyrazolopyrimidine-based drugs enables the exploration of structure-activity relationships and the optimization of drug candidates. This can lead to the discovery of novel compounds with superior pharmacological properties, ultimately contributing to the advancement of cancer treatment options.

Upstream product

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• 1260243-04-6 ethyl 5-amino-1H-pyrazole-4-carboxylate 
• 926663-00-5 5-hydroxypyrazole[1,5-a]pyrimidine-3-carboxylic acid ethyl ester 
• 6994-25-8 3-amino-4-pyrazolecarboxylic acid ethyl ester 

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.

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

Design and synthesis of Imidazo[1,2-b]pyridazine IRAK4 inhibitors for the treatment of mutant MYD88 L265P diffuse large B-cell lymphoma

Harboring MYD88 L265P mutation triggers tumors growth through the activation of NF-κB by interleukin-1 receptor associated kinase 4 (IRAK4) in diffuse large B-cell lymphoma (DLBCL), highlighting IRAK4 as a therapeutic target for tumors driven by aberrant MYD88 signaling. Herein, we report the design, synthesis, and structure?activity relationships of imidazo[1,2-b]pyridazines as potent IRAK4 inhibitors. The representative compound 5 exhibited excellent IRAK4 potency (IRAK4 IC50 = 1.3 nM) and favorable kinase selectivity profile. It demonstrated cellular selectivity for activated B cell–like (ABC) subtype DLBCL with MYD88 L265P mutation in cytotoxicity assay. The kinase inhibitory efficiency of compound 5 was further validated by Western blot analysis of phosphorylation of IRAK4 and downstream signaling in OCI-LY10 and TMD8 cells. Besides, combination of compound 5 and BTK inhibitor ibrutinib synergistically reduced the viability of TMD8 cells. These results indicated that compound 5 could be a promising IRAK4 inhibitor for the treatment of mutant MYD88 DLBCL.