114040-06-1

Basic information

• Product Name: Pyrazolo[1,5-a]pyrimidine, 3-bromo-5,7-dichloro-
• Synonyms: Pyrazolo[1,5-a]pyrimidine, 3-bromo-5,7-dichloro-;3-Bromo-5,7-dichloropyrazolo[1,5-a]pyrimidine
• CAS NO: 114040-06-1
• Molecular Formula: C₆H₂BrCl₂N₃
• Molecular Weight: 266.91
• Product Categories: API intermediates
• Mol File: 114040-06-1.mol
• Article Data: 12

Chemical Properties

• Melting Point: 73-75 °C
• Appearance: /
• Density: 2.16
• Refractive Index: 1.782
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -3.17±0.40(Predicted)
• CAS DataBase Reference: Pyrazolo[1,5-a]pyrimidine, 3-bromo-5,7-dichloro-(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrazolo[1,5-a]pyrimidine, 3-bromo-5,7-dichloro-(114040-06-1)
• EPA Substance Registry System: Pyrazolo[1,5-a]pyrimidine, 3-bromo-5,7-dichloro-(114040-06-1)

Safety Data

• Hazardous Substances Data: 114040-06-1(Hazardous Substances Data)

Usage

Description

Pyrazolo[1,5-a]pyrimidine, 3-bromo-5,7-dichlorois a chemical compound belonging to the class of pyrazolopyrimidines. It is characterized by the presence of a pyrazolo and pyrimidine ring fused together, with a bromo and two chloro substituents at the 3rd and 5th, 7th positions, respectively. Pyrazolo[1,5-a]pyrimidine, 3-bromo-5,7-dichlorois known for its potential applications in the pharmaceutical industry due to its unique structural features and biological activities.

Uses

Used in Pharmaceutical Industry:
Pyrazolo[1,5-a]pyrimidine, 3-bromo-5,7-dichlorois used as an intermediate in the synthesis of inhibitors targeting mitogen-activated protein kinase-activated protein kinase 2 (MAPK-activated protein kinase 2). These inhibitors play a crucial role in the development of anti-inflammatory drugs, as they help modulate the inflammatory response by inhibiting the activation of specific signaling pathways involved in inflammation.
The compound's application in the pharmaceutical industry is primarily due to its ability to serve as a building block for the development of novel anti-inflammatory agents. By targeting MAPK-activated protein kinase 2, these inhibitors can potentially provide relief from various inflammatory conditions and contribute to the advancement of therapeutic options for patients suffering from such ailments.

InChI:InChI=1/C6H2BrCl2N3/c7-3-2-10-12-5(9)1-4(8)11-6(3)12/h1-2H

Upstream product

• 672323-32-9 pyrazolo[1,5-a]pyrimidine-5,7(4H,6H)-dione 
• 57489-70-0 5,7-dihydroxypyrazolo[1,5-a]pyrimidine 
• 57489-77-7 5,7-dichloropyrazolo[1,5-a]pyrimidine 

Downstream Products

• 1610679-97-4 tert-butyl (3-bromo-5-phenoxypyrazolo[1,5-a]pyrimidin-7-yl)((tetrahydro-2H-pyran-4-yl)methyl)carbamate 
• 1610680-37-9 tert-butyl (3-(4-(cyclopropylcarbamoyl)-3-methylphenyl)-5-(phenylsulfonyl)pyrazolo[1,5-a]pyrimidin-7-yl)((tetrahydro-2H-pyran-4-yl)methyl)carbamate 
• 1610680-38-0 tert-butyl (3-bromo-5-(phenylsulfonyl)pyrazolo[1,5-a]pyrimidin-7-yl)((tetrahydro-2H-pyran-4-yl)methyl)carbamate 
• 1610676-69-1 C₂₉H₃₁N₅O₃ 
• 1610677-21-8 (S)-N-cyclopropyl-2-methyl-4-(7-(((tetrahydro-2H-pyran-4-yl)methyl)amino)-5-(((tetrahydrofuran-2-yl)methyl)amino)pyrazolo[1,5-a]pyrimidin-3-yl)benzamide 
• 1610680-39-1 tert-butyl (3-bromo-5-phenoxypyrazolo[1,5-a]pyrimidin-7-yl)((tetrahydro-2Hpyran-4-yl)methyl)carbamate 
• 1610680-43-7 (S)-N-cyclopropyl-2-methyl-4-(7-(((tetrahydro-2H-pyran-4-yl)methyl)amino)-5-(((tetrahydrofuran-2-yl)methyl)amino)pyrazolo[1,5-a]pyrimidin-3-yl)benzamide hydrochloride 
• 1610679-85-0 tert-butyl (3-bromo-5-(((1S,2R)-2-hydroxycyclohexyl)amino)pyrazolo[1,5-a]pyrimidin-7-yl) ((tetrahydro-2H-pyran-4-yl)methyl)carbamate 
• 1610679-11-2 N-cyclopropyl-4-(7-((((1s,4s)-4-hydroxycyclohexyl)methyl)amino)-5-(pyridin-3-yloxy)pyrazolo[1,5-a]pyrimidin-3-yl)-2-methylbenzamide trifluoroacetate 
• 1610677-33-2 N-cyclopropyl-4-(5-(((1S,2R)-2-hydroxycyclohexyl)amino)-7-(((tetrahydro-2H-pyran-4-yl)methyl)amino)pyrazolo[1,5-a]pyrimidin-3-yl)-2-methylbenzamide 
• 1610677-13-8 (R)-N-cyclopropyl-4-(5-((1-hydroxybutan-2-yl)amino)-7-(((tetrahydro-2H-pyran-4-yl)methyl)amino)pyrazolo[1,5-a]pyrimidin-3-yl)-2-methylbenzamide 
• 1610676-75-9 N-cyclopropyl-2-methyl-4-(7-((2-morpholinoethyl)amino)-5-phenoxypyrazolo[1,5-a]pyrimidin-3-yl)benzamide trifluoroacetic acid 
• 1610676-89-5 4-(5-(cyclopentylamino)-7-(((tetrahydro-2H-pyran-4-yl)methyl)amino)pyrazolo[1,5-a]pyrimidin-3-yl)-N-cyclopropyl-2-methylbenzamide trifluoroacetic acid 

Relevant articles and documents

Discovery of Pyrazolo[1,5-a]pyrimidine TTK Inhibitors: CFI-402257 is a Potent, Selective, Bioavailable Anticancer Agent

This work describes a scaffold hopping exercise that begins with known imidazo[1,2-a]pyrazines, briefly explores pyrazolo[1,5-a][1,3,5]triazines, and ultimately yields pyrazolo[1,5-a]pyrimidines as a novel class of potent TTK inhibitors. An X-ray structure of a representative compound is consistent with 11/2 type inhibition and provides structural insight to aid subsequent optimization of in vitro activity and physicochemical and pharmacokinetic properties. Incorporation of polar moieties in the hydrophobic and solvent accessible regions modulates physicochemical properties while maintaining potency. Compounds with enhanced oral exposure were identified for xenograft studies. The work culminates in the identification of a potent (TTK Ki = 0.1 nM), highly selective, orally bioavailable anticancer agent (CFI-402257) for IND enabling studies.

PYRAZOLOPYRIMIDINE COMPOUNDS

The present teachings provide a compound represented by structural formula (1-0), or a pharmaceutically acceptable salt thereof. Also described are pharmaceutical compositions and methods of use thereof.

Erratum: Mitogen-activated protein kinase-activated protein kinase 2 (MAPKAP-K2) as an antiinflammatory target: Discovery and in vivo activity of selective pyrazolo[1,5-a]pyrimidine inhibitors using a focused library and structure-based optimization approach (Journal of Medicinal Chemistry (2012) 55 (6700-6715) DOI: 10.1021/jm300411k)

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