877399-51-4

Basic information

• Product Name: (R)-tert-butyl 4-(4-(6-aMino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
• Synonyms: 1-Piperidinecarboxylic acid,4-[4-[6-aMino-5-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-3-pyridinyl]-1H-pyrazol-1-yl]-, 1,1-diMethylethyl ester;4-[4-[6-Amino-5-[[(R)-1-(2,6-dichloro-3-fluorophenyl)ethyl]oxy]pyridin-3-yl]pyrazol-1-yl]piperidine-1-carboxylic acid tert-butyl ester;(R)-tert-butyl 4-(4-(6-aMino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl);tert-butyl 4-(4-(6-amino-5-((R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate;(R)-tert-butyl 4-(4-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridine -3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate (R)-tert-butyl 4-(4-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridine -3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate;(R)-tert-butyl 4-(4-(6-aMino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate;tert-butyl (R)-4-(4-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
• CAS NO: 877399-51-4
• Molecular Formula: C26H30Cl2FN5O3
• Molecular Weight: 550.4525032
• Mol File: 877399-51-4.mol
• Article Data: 27

Chemical Properties

• Melting Point: 150℃
• Boiling Point: 654.7±55.0 °C(Predicted)
• Appearance: /
• Density: 1.38±0.1 g/cm3 (20 oC 760 Torr), Calc.*
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 7.11±0.10(Predicted)
• CAS DataBase Reference: (R)-tert-butyl 4-(4-(6-aMino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-tert-butyl 4-(4-(6-aMino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate(877399-51-4)
• EPA Substance Registry System: (R)-tert-butyl 4-(4-(6-aMino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate(877399-51-4)

Safety Data

• Hazardous Substances Data: 877399-51-4(Hazardous Substances Data)

Usage

General Description

The chemical "(R)-tert-butyl 4-(4-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate" is a complex compound with a molecular structure that includes a tert-butyl group, a piperidine-1-carboxylate group, and multiple pyridin and pyrazol groups. This chemical is widely used in pharmaceutical research and drug development due to its potential as a therapeutic agent. The specific arrangement of its functional groups and chiral center make it a target for studying structure-activity relationships and for designing novel drugs with targeted biological activities. Further research on this compound may lead to the development of new treatments for various medical conditions.

Upstream product

• 877399-74-1 tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate 
• 1448326-33-7 (S)-5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-aminopyridine 
• 74115-13-2 5-bromopyridine-3-ol 
• 691872-15-8 5-bromo-3-hydroxy-2-nitropyridine 
• 756503-69-2 (±)-5-bromo-3-(1-(2,6-dichloro-3-fluoropheny)ethoxy)pyridin-2-amine 
• 290835-85-7 2',6'-dichloro-3'-fluoroacetophenone 
• 1331786-34-5 (±)-bis(Boc)-3-(1-(2,6-dichloro-3-fluoropheny)ethoxy)-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-2-amine 
• 1331786-33-4 (±)-bis(Boc)-5-bromo-3-(1-(2,6-dichloro-3-fluoropheny)ethoxy)pyridin-2-amine 
• 756520-67-9 (±)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine 
• 756521-08-1 (±)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-nitropyridine 
• 756520-66-8 1-(2,6-dichloro-3-fluorophenyl)ethanol 
• 877399-08-1 (±)-3-(1-(2,6-dichloro-3-fluoropheny)ethoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine 
• 877399-50-3 4-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester 
• 756509-08-7 3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(1H-pyrazol-4-yl)pyridin-2-amine 

Downstream Products

• 877399-52-5 crizotinib 

Relevant articles and documents

Mild and Robust Stille Reactions in Water using Parts Per Million Levels of a Triphenylphosphine-Based Palladacycle

An inexpensive and new triphenylphosphine-based palladacycle has been developed as a pre-catalyst, leading to highly effective Stille cross-coupling reactions in water under mild reaction conditions. Only 500–1000 ppm of Pd suffices for couplings involving a variety of aryl/heteroaryl halides with aryl/hetaryl stannanes. Several drug intermediates can be prepared using this catalyst in aqueous nanoreactors formed by 2 wt % Brij-30 in water.

Development and biological investigations of hypoxia-sensitive prodrugs of the tyrosine kinase inhibitor crizotinib

Despite the huge success of tyrosine kinase inhibitors as anticancer agents, severe side effects are a major problem. In order to overcome this drawback, the first hypoxia-activatable 2-nitroimidazole-based prodrugs of the clinically approved ALK and c-MET inhibitor crizotinib were developed. The 2-aminopyridine functionality of crizotinib (essential for target kinase binding) was considered as ideal position for prodrug derivatization. Consequently, two different prodrugs were synthesized with the nitroimidazole unit attached to crizotinib either via carbamoylation (A) or alkylation (B) of the 2-aminopyridine moiety. The successful prodrug design could be proven by docking studies and a dramatically reduced ALK and c-MET kinase-inhibitory potential. Furthermore, the prodrugs showed high stability in serum and release of crizotinib in an enzymatic nitroreductase-based cleavage assay was observed for prodrug A. The in vitro activity of both prodrugs was investigated against ALK- and c-MET-dependent or –overexpressing cells, revealing a distinct hypoxia-dependent activation for prodrug A. Finally, inhibition of c-MET phosphorylation and cell proliferation could also be proven in vivo. In summary of the theoretical, chemical and biological studies, prodrug derivatization of the 2-aminopyridine position can be considered as a promising strategy to reduce the side effects and improve the anticancer activity of crizotinib.

Palladium removal method for crizotinib intermediate

The invention discloses a method for removing palladium from a crizotinib intermediate. The method comprises the following steps: adding a heavy metal ion remover into a palladium-containing reactionsolution; after the remover is separated, a solid is sep