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

Uses

3-Bromo-5,7-dichloro-pyrazolo[1,5-a]pyrimidine is an intermediate used in the synthesis of inhibitors of mitogen-activated protein kinase-activated protein kinase 2 as an antiinflammatory target.

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 
• 57489-77-7 5,7-dichloropyrazolo[1,5-a]pyrimidine 
• 57489-70-0 5,7-dihydroxypyrazolo[1,5-a]pyrimidine 

Downstream Products

• 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 
• 1610680-13-1 tert-butyl (3-bromo-5-(3-fluorophenoxy)pyrazolo[1,5-a]pyrimidin-7-yl)(2-morpholinoethyl)carbamate 
• 1610680-02-8 tert-butyl (3-bromo-5-phenoxypyrazolo[1,5-a]pyrimidin-7-yl)(2-morpholinoethyl)carbamate 

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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