1146629-83-5

Basic information

• Product Name: (R)-3-(4-broMo-1H-pyrazol-1-yl)-3-cyclopentylpropanenitrile
• Synonyms: (R)-3-(4-broMo-1H-pyrazol-1-yl)-3-cyclopentylpropanenitrile;1H-Pyrazole-1-propanenitrile, 4-broMo-b-cyclopentyl-, (bR)-;(betaR)-4-Bromo-beta-cyclopentyl-1H-pyrazole-1-propanenitrile;(3R)-3-(4-bromopyrazol-1-yl)-3-cyclopentylpropanenitrile
• CAS NO: 1146629-83-5
• Molecular Formula: C₁₁H₁₄BrN₃
• Molecular Weight: 268.15296
• Mol File: 1146629-83-5.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 394.2±22.0 °C(Predicted)
• Appearance: /
• Density: 1.51±0.1 g/cm3(Predicted)
• PKA: -0.17±0.10(Predicted)
• CAS DataBase Reference: (R)-3-(4-broMo-1H-pyrazol-1-yl)-3-cyclopentylpropanenitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-(4-broMo-1H-pyrazol-1-yl)-3-cyclopentylpropanenitrile(1146629-83-5)
• EPA Substance Registry System: (R)-3-(4-broMo-1H-pyrazol-1-yl)-3-cyclopentylpropanenitrile(1146629-83-5)

Safety Data

• Hazardous Substances Data: 1146629-83-5(Hazardous Substances Data)

Usage

General Description

(R)-3-(4-bromo-1H-pyrazol-1-yl)-3-cyclopentylpropanenitrile is a chemical compound that belongs to the class of nitriles. It is a derivative of pyrazole, which is a five-membered aromatic heterocyclic compound containing nitrogen. The presence of the bromine atom and the nitrile group in the molecule gives it unique chemical properties and potential biological activities. (R)-3-(4-broMo-1H-pyrazol-1-yl)-3-cyclopentylpropanenitrile may be used in the development of pharmaceuticals or agrochemicals due to its structural features, and it may also be used as a reagent in various chemical reactions. Overall, the compound has potential applications in medicinal chemistry and other fields requiring the synthesis of unique organic molecules.

Upstream product

• 1146629-82-4 (3R)-3-(4-bromo-1H-pyrazol-1-yl)-3-cyclopentylpropanal 
• 95882-33-0 3-cyclopentyl-3-oxopropanenitrile 
• 136823-41-1 methyl 3-cyclopentylacrylate 
• 872-53-7 cyclopentanealdehyde 
• 137-43-9 Cyclopentyl bromide 
• 2075-45-8 4-bromo-1H-pyrazole 
• 4630-80-2 methyl cyclopentane carboxylate 
• 54125-23-4 cyclopentylallene 

Downstream Products

• 1146629-84-6 (3R)-3-cyclopentyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propanenitrile 
• 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.

Intermediate of JAK inhibitor, and preparation method thereof

The present invention relates to a novel key intermediate of a JAK inhibitor ruxolitinib, and a preparation method thereof, wherein the chemical name of the intermediate is (R)-3-(4-boric acid-1H-pyrazole-1-yl)-3-cyclopentylpropionitrile. According to the present invention, the new ruxolitinib preparation route is provided, wherein each reaction of the route has the high yield, the total yield ofthe route is high, the purity of the obtained product is good, the post-treatment of the reaction is simple, and column chromatography is not required; by adopting the route, the required raw materials or catalysts and other materials are relatively easy to obtain; and compared to the method in the prior art, the method of the present invention is economical and is suitable for industrial production.

A Russo advantage for Nepal synthesis of intermediates method (by machine translation)

The invention relates to a Russo advantage for Nepal synthesis of intermediates method, first of all by the cyclopentane carboxylic acid methyl ester and acetonitrile catalytic reaction preparation 3 - cyclopentyl - 3 - oxo third nitrile, then 3 - cyclopentyl - 3 - oxo third nitrile enzyme catalytic asymmetric reduction to generate chiral alcohols (S) - 3 - cyclopentyl - 3 - hydroxy propionitrile; (S) - 3 - cyclopentyl - 3 - hydroxy propionitrile by the Mitsunobu reaction and 4 - bromine pyrazole coupling get Russo advantage for Nepal intermediate (3R) - 3 - (4 - bromo - 1H - pyrazole - 1 - yl) - 3 - cyclopentane isopropyl amine; the synthesis method has the short route, the cost is low, mild condition, stereoselectivity is good, is suitable for the industrial production of the advantages. (by machine translation)