78064-96-7

Usage

Uses

Used in Organic Synthesis:
4-(PYRROLIDIN-1-YLMETHYL)BENZONITRILE is used as a key intermediate in organic synthesis for its ability to contribute to the formation of complex organic molecules. Its unique structure allows it to be a versatile component in the synthesis of various compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 4-(PYRROLIDIN-1-YLMETHYL)BENZONITRILE is utilized as a building block in the development of new drugs. Its properties make it suitable for the creation of molecules with potential therapeutic applications.
Used in Agrochemical Development:
4-(PYRROLIDIN-1-YLMETHYL)BENZONITRILE also finds application in the agrochemical sector, where it serves as a component in the synthesis of compounds used in agricultural chemicals, potentially contributing to the development of new pesticides or other agrochemical products.
Used in the Production of Fine Chemicals:
4-(PYRROLIDIN-1-YLMETHYL)BENZONITRILE is used as an intermediate in the production of various fine chemicals, indicating its importance in the synthesis of high-purity and high-value chemical products.
Used in Medicinal Chemistry:
With potential applications in medicinal chemistry, 4-(PYRROLIDIN-1-YLMETHYL)BENZONITRILE is employed in the research and development of pharmaceuticals, highlighting its significance in the discovery of new medicines and therapeutic agents.

InChI:InChI=1/C12H14N2/c13-9-11-3-5-12(6-4-11)10-14-7-1-2-8-14/h3-6H,1-2,7-8,10H2/p+1

Upstream product

• 123-75-1 pyrrolidine 
• 105-07-7 4-cyanobenzaldehyde 
• 17201-43-3 4-cyanobenzyl bromide 
• 104-94-9 4-methoxy-aniline 
• 874-89-5 4-Cyanobenzyl alcohol 
• 609-36-9 rac-Pro-OH 
• 28525-13-5 4-(phenylsulfonyl)benzonitrile 
• 54600-29-2 1-((trimethylsilyl)methyl)pyrrolidine 
• 623-00-7 4-bromobenzenecarbonitrile 
• 120-94-5 1-Methylpyrrolidine 
• 623-03-0 4-Cyanochlorobenzene 

Downstream Products

• 650628-72-1 4-[(pyrrolidin-1-yl)methyl]-benzaldehyde 
• 1613436-04-6 5-methyl-3-(4-(pyrrolidin-1-ylmethyl)phenyl)isoquinolin-1(2H)-one hydrochloride 
• 1454898-07-7 5-methyl-3-(4-(pyrrolidin-1-ylmethyl)phenyl)isoquinolin-1(2H)-one 
• 1414782-05-0 7-amino-3-(4-(pyrrolidin-1-ylmethyl)benzyl)quinazolin-4(3H)-one 
• 1414781-98-8 C₂₉H₂₆ClN₅O 
• 1414782-04-9 N-(4-(pyrrolidin-1-ylmethyl)benzyl)-2-amino-4-nitrobenzamide 
• 91271-79-3 N-((4-(pyrrolidin-1-ylmethyl)phenyl)methyl)amine 

Relevant academic research and scientific papers

Metal-Free Aminomethylation of Aromatic Sulfones Promoted by Eosin Y

A metal-free α-aminomethylation of heteroaryls promoted by eosin Y under green light irradiation is reported. A large variety of α-trimethylsilylamines as precursor of α-aminomethyl radical species were engaged to functionalize sulfonyl-heteroaryls following a Homolytic Aromatic Substitution (HAS) pathway. This method has provided a range of α-aminoheteroaryl compounds including a functionalized natural product. The mechanism of this late-stage functionalization of aryls was investigated and suggests the formation of a sulfonyl radical intermediate over a reductive quenching cycle.

Development of inhibitors against mycobacterium abscessus tRNA (m1G37) Methyltransferase (TrmD) Using Fragment-Based Approaches

Mycobacterium abscessus (Mab) is a rapidly growing species of multidrug-resistant nontuberculous mycobacteria that has emerged as a growing threat to individuals with cystic fibrosis and other pre-existing chronic lung diseases. Mab pulmonary infections are difficult, or sometimes impossible, to treat and result in accelerated lung function decline and premature death. There is therefore an urgent need to develop novel antibiotics with improved efficacy. tRNA (m1G37) methyltransferase (TrmD) is a promising target for novel antibiotics. It is essential in Mab and other mycobacteria, improving reading frame maintenance on the ribosome to prevent frameshift errors. In this work, a fragment-based approach was employed with the merging of two fragments bound to the active site, followed by structure-guided elaboration to design potent nanomolar inhibitors against Mab TrmD. Several of these compounds exhibit promising activity against mycobacterial species, including Mycobacterium tuberculosis and Mycobacterium leprae in addition to Mab, supporting the use of TrmD as a target for the development of antimycobacterial compounds.

Ruthenium and Iron-Catalysed Decarboxylative N-alkylation of Cyclic Α-Amino Acids with Alcohols: Sustainable Routes to Pyrrolidine and Piperidine Derivatives

A modular and waste-free strategy for constructing N-substituted cyclic amines via decarboxylative N-alkylation of α-amino acids employing ruthenium- and iron-based catalysts is presented. The reported method allows the synthesis of a wide range of five- and six-membered N-alkylated heterocycles in moderate-to-excellent yields starting from predominantly proline and a broad range of benzyl alcohols, and primary and secondary aliphatic alcohols. Examples using pipecolic acid for the construction of piperidine derivatives, as well as the one-pot synthesis of α-amino nitriles, are also shown.

Dehydrogenative Aromatization and Sulfonylation of Pyrrolidines: Orthogonal Reactivity in Photoredox Catalysis

Oxidative dehydrogenative aromatization and selective sulfonylation reactions of N-heterocycles under visible-light photoredox catalysis were established. The mild reaction conditions make this approach an appealing and versatile strategy to functionalize/oxidize pyrrolidines whereby arylsulfonyl chlorides were identified to be both catalyst regeneration and sulfonylation reagents.

Hydrogen-free reductive amination using iron pentacarbonyl as a reducing agent

We developed solvent-free reductive amination without an external hydrogen source using iron pentacarbonyl as a reducing agent. Neither a catalyst nor any other additives were employed. Various types of substrates are suitable for the reaction, including

tert-Butoxy-Radical-Promoted α-Arylation of Alkylamines with Aryl Halides

In the presence of a tert-butoxy radical precursor, the reaction of alkylamines with aryl halides was found to give α-arylated alkylamines through homolytic aromatic substitution of the halogen atoms.

Exploration of the nicotinamide-binding site of the tankyrases, identifying 3-arylisoquinolin-1-ones as potent and selective inhibitors in vitro

Tankyrases-1 and -2 (TNKS-1 and TNKS-2) have three cellular roles which make them important targets in cancer. Using NAD+ as a substrate, they poly(ADP-ribosyl)ate TRF1 (regulating lengths of telomeres), NuMA (facilitating mitosis) and axin (in wnt/β-catenin signalling). Using molecular modelling and the structure of the weak inhibitor 5-aminoiso quinolin-1-one, 3-aryl-5-substituted-isoquinolin-1-ones were designed as inhibitors to explore the structure-activity relationships (SARs) for binding and to define the shape of a hydrophobic cavity in the active site. 5-Amino-3-arylisoquinolinones were synthesised by Suzuki-Miyaura coupling of arylboronic acids to 3-bromo-1-methoxy-5-nitro-isoquinoline, reduction and O-demethylation. 3-Aryl-5-methylisoquinolin-1-ones, 3-aryl-5-fluoroisoquinolin-1-ones and 3-aryl-5-methoxyisoquinolin-1-ones were accessed by deprotonation of 3-substituted-N,N,2-trimethylbenzamides and quench with an appropriate benzonitrile. SAR around the isoquinolinone core showed that aryl was required at the 3-position, optimally with a para-substituent. Small meta-substituents were tolerated but groups in the ortho-positions reduced or abolished activity. This was not due to lack of coplanarity of the rings, as shown by the potency of 4,5-dimethyl-3-phenylisoquinolin-1-one. Methyl and methoxy were optimal at the 5-position. SAR was rationalised by modelling and by crystal structures of examples with TNKS-2. The 3-aryl unit was located in a large hydrophobic cavity and the para-substituents projected into a tunnel leading to the exterior. Potency against TNKS-1 paralleled potency against TNKS-2. Most inhibitors were highly selective for TNKSs over PARP-1 and PARP-2. A range of highly potent and selective inhibitors is now available for cellular studies.

Reductive amination without an external hydrogen source

A method of reductive amination without an external hydrogen source is reported. Carbon monoxide is used as the reductant. The reaction proceeds efficiently for a variety of carbonyl compounds and amines at low catalyst loadings and is mechanistically interesting as it does not seem to involve molecular hydrogen. Look, no H2! Reductive amination without an external hydrogen source has been developed using carbon monoxide as the reductant and rhodium acetate (0.2-1mol %) as catalyst. The method tolerates a variety of functional groups and provides target amines in good to excellent yields.

Mimicking the intramolecular hydrogen bond: Synthesis, biological evaluation, andmolecular modeling of benzoxazines and quinazolines as potential antimalarial agents

The intramolecular hydrogen bond formed between a protonated amine and a neighboring H-bond acceptor group in the side chain of amodiaquine and isoquine is thought to play an important role in their antimalarial activities. Here we describe isoquine-based

6-ARYLALKYLAMINO- 2,3,4,5-TETRAHYDRO-1H-BENZO[D]AZEPINES AS 5-HT2C RECEPTOR AGONISTS

The present invention provides 6-substituted 2,3,4,5-tetrahydro-lH- benzo[d]azepines of Formula (I) as selective 5-HT2c receptor agonists for the treatment of 5-HT2c associated disorders including obesity, obsessive/compulsive disorder, depression, and anxiety, where, R6 is -NR10R11, where R10 is substituted phenylalkyl or substituted pyridylalkyl and other substituents are as defined in the specification.