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Usage

Uses

Used in Pharmaceutical Industry:
Cyclopentanecarbonitrile, 2-amino(9CI) is used as a key intermediate in the synthesis of certain pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
Cyclopentanecarbonitrile, 2-amino(9CI) is used as a precursor in the production of various agrochemicals, including pesticides and insecticides. Its ability to form nitrogen-containing organic compounds makes it an essential component in the development of effective and environmentally friendly agricultural products.
Used in Organic Chemistry Research:
Cyclopentanecarbonitrile, 2-amino(9CI) is also used as a starting material in the synthesis of other nitrogen-containing organic compounds, contributing to the advancement of organic chemistry and the discovery of new chemical entities with potential applications in various industries.

Upstream product

• 111-69-3 hexanedinitrile 
• 2321-76-8 2-iminocyclopentanecarbonitrile 
• 2941-23-3 2-amino-1-cyanocyclopentene 

Downstream Products

• 21544-02-5 2-(aminomethyl)-cyclopentylamine 
• 924669-64-7 2-((6-chloropyridin-3-yl)methylamino)cyclopentanecarbonitrile 
• 472966-14-6 tert-butyl (2-cyanocyclopentyl)carbamate 
• 1418199-98-0 trans-2-[6-benzenesulfonyl-2-((R)-1-hydroxy-ethyl)-6H-1,3,5,6-tetraaza-as-indacen-1-yl]-cyclopentanecarbonitrile 

Relevant academic research and scientific papers

FUSED TRICYCLIC COMPOUNDS FOR USE AS INHIBITORS OF JANUS KINASES

The invention provides novel compounds of formula (I) having the general formula (I) wherein R1, V, W, X, Y and Z are as described herein. Accordingly, the compounds may be provided in pharmaceutically acceptable compositions and used for the treatment of immunological or hyperproliferative disorders.

Syntheses and biological activities of octahydro-1H-cyclopenta[d]pyrimidine derivatives

Various nitromethylene derivatives were synthesized regioselectively. Compounds 8a-f were obtained by the reaction of 1-((5-chloropyridin-2-yl)methyl) -2-(nitromethylene)-octahydro-1H-cyclopenta[d]-pyrimidine (3) with primary amines and formaldehyde. The synthesized compounds were identified by 1H NMR, HRMS (EI), and IR, and preliminary bioassays indicated that most of them showed moderate insecticidal activities against Aphis craccivora. The relationship between hydrophobicity and biological activity was also discussed.

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.

Assisted hydrolysis of cis-2-(3-phenylthioureido)cyclopentane-carbonitrile in alkaline solution. Solvent dependent switch from hydrolysis to rearrangement of the iminothiooxopyrimidine intermediate

The cis and trans isomers of 2-(3-phenylthioureido)cyclopentanecarbonitrile, 1, and the respective carboxamides, 3, and acids, 4, have been prepared. Acid cyclization of both nitriles, faster with the cis isomer, gave the more stable cis-2-thiooxo-cyclopenta[d]pyrimidin-4-one, 7. In base cis-1 formed the cis 4-imino-2-thiooxopyrimidine 2 which in aqueous alkali broke down via 3 to the acid 4; while in the presence of 66% acetonitrile 2 rearranged to the 4-phenyliminopyrimidine 5 to give as final product the thioureido acid 6 carrying no phenyl group. The 1H NMR data for imino and phenylimino derivatives 2 and 5 showed strong bias for conformation A with 1-N pseudoaxial in the cyclopentane ring. Spectra of the E and Z isomers of the iminopyrimidine 2 under slow exchange could be recorded in DMSO-d6. The phenylimino tautomer of 5 is observed in CD3OD and in CDCl3 with the E and Z isomers in a 1:1 ratio. In DMSO-d6 the phenylamino tautomer 5a is also detected. The first process in aqueous KOH, the conversion of nitrile cis-1 into the imino intermediate 2, reaches an equilibrium which shifts towards the nitrile at higher alkalinities because of ionization of the phenylthioureido group (Ke = [2]/[1] = 2.43 and pKAH = 12.74). The cyclization of 1 to 2 is first order in [OH-] while the slower breakdown of 2 is pH independent. The latter is 104 times faster than the hydrolysis of acetonitrile evidencing substantial anchimeric assistance. The change in the reaction route towards the rearranged phenyliminopyrimidine 5 upon addition of acetonitrile can be caused by the lower dielectric constant favouring the elimination step leading to the intermediate isothiocyanate, and by increased activity of OH- accelerating the (presumably) second order elimination step as opposed to the ph-independent hydrolysis of the imino derivative 2.