1146629-84-6

Basic information

• Product Name: (R)-3-cyclopentyl-3-(4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile
• Synonyms: (R)-3-Cyclopentyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitri;(betaR)-beta-Cyclopentyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-propanenitrile;(R)-3-Cyclopentyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propaneni;(R)-3-cyclopentyl-3-(4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile;1H-Pyrazole-1-propanenitrile, b-cyclopentyl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-, (bR)-
• CAS NO: 1146629-84-6
• Molecular Formula: C₁₇H₂₆BN₃O₂
• Molecular Weight: 315.21824
• Mol File: 1146629-84-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 471.8±25.0 °C(Predicted)
• Appearance: /
• Density: 1.13±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 1.71±0.10(Predicted)
• CAS DataBase Reference: (R)-3-cyclopentyl-3-(4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-cyclopentyl-3-(4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile(1146629-84-6)
• EPA Substance Registry System: (R)-3-cyclopentyl-3-(4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile(1146629-84-6)

Safety Data

• Hazardous Substances Data: 1146629-84-6(Hazardous Substances Data)

Usage

General Description

This chemical "(R)-3-cyclopentyl-3-(4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile" is a complex organic compound which plays an important role in the realm of synthetic chemistry. The molecule encompasses several functional groups, including a dioxaborolane group that is known for its uses in Suzuki-Miyaura cross-coupling reactions, a versatile method for forming carbon-carbon bonds. The molecule also contains a nitrile group that introduce polarity and reactivity, and it also provides the molecule potential biological properties. It has a pyrazole moiety, which is a component of various pharmacologically active compounds, coupled with a cyclopentyl group, a common piece in bioactive molecules, that enhances lipophilicity. Ultimately, the specific properties and usage of this compound would depend on its chemical context.

Upstream product

• 136823-41-1 methyl 3-cyclopentylacrylate 
• 54125-23-4 cyclopentylallene 
• 1146629-82-4 (3R)-3-(4-bromo-1H-pyrazol-1-yl)-3-cyclopentylpropanal 
• 1153949-38-2 racemic-3-cyclopentyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile 
• 73183-34-3 bis(pinacol)diborane 
• 1146629-83-5 (R)-3-(4-bromo-1H-pyrazol-1-yl)-3-cyclopentylpropanecarbonitrile 

Downstream Products

• 941678-49-5 ruxolitinib 

Relevant articles and documents

Structural Insights into JAK2 Inhibition by Ruxolitinib, Fedratinib, and Derivatives Thereof

The discovery that aberrant activity of Janus kinase 2 (JAK2) is a driver of myeloproliferative neoplasms (MPNs) has led to significant efforts to develop small molecule inhibitors for this patient population. Ruxolitinib and fedratinib have been approved for use in MPN patients, while baricitinib, an achiral analogue of ruxolitinib, has been approved for rheumatoid arthritis. However, structural information on the interaction of these therapeutics with JAK2 remains unknown. Here, we describe a new methodology for the large-scale production of JAK2 from mammalian cells, which enabled us to determine the first crystal structures of JAK2 bound to these drugs and derivatives thereof. Along with biochemical and cellular data, the results provide a comprehensive view of the shape complementarity required for chiral and achiral inhibitors to achieve highest activity, which may facilitate the development of more effective JAK2 inhibitors as therapeutics.

PROCESSES FOR PREPARING JAK INHIBITORS AND RELATED INTERMEDIATE COMPOUNDS

The present invention is related to processes for preparing chiral substituted pyrazolyl pyrrolo[2,3-d]pyrimidines of Formula III, and related synthetic intermediate compounds. The chiral substituted pyrazolyl pyrrolo[2,3-d]pyrimidines are useful as inhibitors of the Janus Kinase family of protein tyrosine kinases (JAKs) for treatment of inflammatory diseases, myeloproliferative disorders, and other diseases.