874293-75-1

Basic information

• Product Name: cis-2-AMinocyclopentanecarbonitrile
• Synonyms: cis-2-AMinocyclopentanecarbonitrile;cis-2-Aminocyclopentane-1-carbonitrile
• CAS NO: 874293-75-1
• Molecular Formula: C6H10N2
• Molecular Weight: 110.157
• Product Categories: Miscellaneous Reagents
• Mol File: 874293-75-1.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: cis-2-AMinocyclopentanecarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: cis-2-AMinocyclopentanecarbonitrile(874293-75-1)
• EPA Substance Registry System: cis-2-AMinocyclopentanecarbonitrile(874293-75-1)

Safety Data

• Hazardous Substances Data: 874293-75-1(Hazardous Substances Data)

Usage

Description

cis-2-Aminocyclopentanecarbonitrile is an organic compound with the chemical formula C6H10N2. It is a key intermediate in the synthesis of various pharmaceuticals and organic compounds.

Uses

Used in Pharmaceutical Industry:
cis-2-Aminocyclopentanecarbonitrile is used as a key intermediate in the preparation of novel 8-oxo-pyridooyrimidine Jak1/2 inhibitors. These inhibitors are important in the development of drugs for the treatment of various diseases, including cancer and autoimmune disorders.
Used in Organic Synthesis:
cis-2-Aminocyclopentanecarbonitrile is also used in the synthesis of alicyclic β-amino nitriles. These compounds are valuable building blocks in the preparation of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals.

Upstream product

• 2941-23-3 2-amino-1-cyanocyclopentene 
• 2321-76-8 2-iminocyclopentanecarbonitrile 
• 111-69-3 hexanedinitrile 
• 874294-11-8 cis-2-aminocyclopentanecarbonitrile 
• 371-27-7 2,2,2-trifluoroethylbutyrate 
• 874294-11-8 trans-2-aminocyclopentanecarbonitrile 

Downstream Products

• 924669-64-7 2-((6-chloropyridin-3-yl)methylamino)cyclopentanecarbonitrile 
• 874294-11-8 trans-2-aminocyclopentanecarbonitrile 
• 874294-11-8 cis-2-aminocyclopentanecarbonitrile 

Relevant articles and documents

An effective approach to the enantiomers of alicyclic β-aminonitriles by using lipase catalysis

Lipase-catalyzed N-acylations of racemic cis- and trans-2- aminocyclopentane- (and cyclohexane-) carbonitriles with 2,2,2-trifluoethyl butanoate in tert-butyl methyl ether (TBME) and in room-temperature ionic liquids (RTILs) were studied. The racemates were effectively resolved (E >200) on a preparative scale by lipase PS-C II (lipase from Burkholderia cepacia) in TBME, resulting in two enantiomers in their enantiopure forms at 50% conversion. The reactions in RTILs with Novozym 435 (Candida antarctica lipase B) were slow and proceeded with low enantioselectivity.

PYRROLOPYRAZINE DERIVATIVES AS SYK AND JAK INHIBITORS

The present invention relates to the use of novel pyrrolopyrazine derivatives of Formula (I), wherein the variables Q and R1 and R2 are defined as described herein, which inhibit JAK and SYK and are useful for the treatment of auto-immune and inflammatory diseases.

Synthesis and microbial transformation of β-amino nitriles

Rhodococcus equi A4, Rhodococcus erythropolis NCIMB 11540 and Rhodococcus sp. R312 were investigated towards their ability to produce β-amino amides and acids from β-amino nitriles. The microorganisms show comparable trends: five-membered alicyclic 2-amino nitriles were transformed significantly faster than the six-membered compounds and the products of trans-2-amino nitriles (amides and acids) were formed considerably faster than the cis-counterparts (amides). The trans-five membered nitriles gave the amides (1b, 5b) in excellent enantiomeric excess (94-99%), the biotransformation of trans-six membered substrates resulted in the formation of the acid (3c, 7c) in excellent ee (87-99%). The ee's of the cis-compounds were throughout lower. Fifteen new substances were synthesized and characterized in the course of this work.