3010-05-7

Usage

Uses

Used in Pharmaceutical Industry:
2-(benzylamino)acetonitrile is utilized as a building block for the preparation of various pharmaceuticals. Its unique structure allows it to be a key component in the synthesis of a range of medicinal compounds, contributing to the development of new drugs.
Used in Agrochemical Industry:
In the agrochemical sector, 2-(benzylamino)acetonitrile serves as a crucial intermediate in the synthesis of agrochemicals. Its application aids in the production of effective pesticides and other agricultural chemicals that are vital for crop protection and yield enhancement.
Used in Organic Synthesis:
2-(benzylamino)acetonitrile is employed as a reagent in organic synthesis, particularly for the preparation of heterocycles and other complex organic compounds. Its versatility in chemical reactions makes it an indispensable tool in the synthesis of fine chemicals.
Used in Drug Discovery and Development:
Owing to its potential medicinal properties, including anti-inflammatory and anti-cancer activities, 2-(benzylamino)acetonitrile is used in drug discovery and development. Researchers leverage its chemical structure to design and develop new therapeutic agents targeting various diseases and conditions.
It is important to follow proper safety precautions and handling procedures when working with 2-(benzylamino)acetonitrile to ensure the well-being of individuals and the environment.

InChI:InChI=1/C9H10N2/c10-6-7-11-8-9-4-2-1-3-5-9/h1-5,11H,7-8H2

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 2547-66-2 1,3,5-Tribenzyl-1,3,5-triazacyclohexane 
• 50-00-0 formaldehyd 
• 151-50-8 potassium cyanide 
• 100-46-9 benzylamine 
• 107-14-2 chloroacetonitrile 
• 590-17-0 cyanomethyl bromide 
• 460-19-5 ethanedinitrile 
• 773837-37-9 sodium cyanide 
• 103-67-3 benzyl-methyl-amine 
• 6343-54-0 N-benzylformamide 
• 7726-87-6 methacryloyloxy-acetonitrile 

Downstream Products

• 67513-57-9 N-Acetoacetyl-N-benzylaminoacetonitril 
• 109040-00-8 1-(Cyanomethyl-benzyl-amino)-1-desoxy-D-fructose 
• 25468-43-3 N-benzyl-N-pentylamine 
• 60508-94-3 Benzyl-(2-methyl-butyl)-amine 
• 91475-76-2 Benzyl-[1,3]dithian-2-ylmethyl-amine 
• 96617-35-5 [Benzyl-(2-oxo-cyclobutyl)-amino]-acetonitrile 
• 134563-39-6 2-Benzoyl-N-benzyl-N-cyanomethyl-benzamide 
• 83196-16-1 [Benzyl-((R)-2-oxo-cyclopentyl)-amino]-acetonitrile 
• 83196-16-1 (+/-)-2-cyclopentanone 
• 94459-04-8 2-Benzyl-2-aza-spiro[3.5]nonan-1-one 
• 94459-11-7 3-Amino-1-benzyl-azetidin-2-one 
• 91475-74-0 N-benzyl-2,2-dimethylpropan-1-amine 
• 91475-75-1 Benzyl-(2-ethoxy-allyl)-amine 
• 103-49-1 dibenzylamine 

Relevant academic research and scientific papers

EIF4E INHIBITORS AND USES THEREOF

The present invention provides compounds inhibiting elF4E activity and compositions and methods of using thereof.

Dynamics in Catalytic Asymmetric Diastereoconvergent (3 + 2) Cycloadditions with Isomerizable Nitrones and α-Keto Ester Enolates

Reaction design in asymmetric catalysis has traditionally been predicated on a structurally robust scaffold in both substrates and catalysts, to reduce the number of possible diastereomeric transition states. Herein, we present the stereochemical dynamics in the Ni(II)-catalyzed diastereoconvergent (3 + 2) cycloadditions of isomerizable nitrile-conjugated nitrones with α-keto ester enolates. Even in the presence of multiple equilibrating species, the catalytic protocol displays a wide substrate scope to access a range of CN-containing building blocks bearing adjacent stereocenters with high enantio- and diastereoselectivities. Our computational investigations suggest that the enantioselectivity is governed in the deprotonation process to form (Z)-Ni-enolates, while the unique syn addition is mainly controlled by weak noncovalent bonding interactions between the nitrone and ligand.

Iron-catalyzed reductive strecker reaction

Strecker reaction is widely applied for the synthesis of amino acids from aldehydes, amines and cyanides. Herein, we report the FeI2-catalyzed reductive Strecker type reaction of formamides instead of aldehydes to produce amino acetonitriles. The challenging capture of carbinolamine intermediates by CN? was achieved via Fe catalysis. This approach afforded better yields than the use of Ir- or Rh-catalysts. The application ability of this methodology is demonstrated by 1) one-pot construction of (13C labeled) complex molecules from CO2 via amino acetonitrile intermediates and 2) convenient production of homologated carboxylic acids from aldehydes.

Access to N-Carbonyl Derivatives of Iminosydnones by Carbonylimidazolium Activation

A new methodology for N-exocyclic functionalization of iminosydnones was developed involving the addition of a large variety of nucleophiles on carbonyl-imidazolium-activated iminosydnones. This practical and highly versatile method provided access to new classes of iminosydnones and opened a straightforward synthetic route to prepare iminosydnone-based prodrugs.

Design and optimization of a series of 4-(3-azabicyclo[3.1.0]hexan-3-yl)pyrimidin-2-amines: Dual inhibitors of TYK2 and JAK1

Herein, we disclose a new series of TYK2/ JAK1 inhibitors based upon a 3.1.0 azabicyclic substituted pyrimidine scaffold. We illustrate the use of structure-based drug design for the initial design and subsequent optimization of this series of compounds. One advanced example 19 met program objectives for potency, selectivity and ADME, and demonstrated oral activity in the adjuvant-induced arthritis rat model.

QUINAZOLINE DERIVATIVES AS ANTITUMOR AGENTS

The present application relates to novel quinazoline compounds as inhibitors of type I receptor tyrosine kinases, the pharmaceutical compositions comprising one or more of the compounds and salts thereof as an active ingredient, and the use of the compounds and salts thereof in the treatment of hyperproliferative diseases, such as cancer and inflammation, in mammals and especially in humans.

SPIRO-LACTAM NMDA MODULATORS AND METHODS OF USING SAME

Disclosed are compounds having potency in the modulation of NMDA receptor activity. Such compounds can be used in the treatment of conditions such as depression and related disorders. Orally delivered formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed.

Controllable access to multi-substituted imidazoles: Via palladium(II)-catalyzed C-C coupling and C-N condensation cascade reactions

A novel and efficient protocol for the synthesis of various 2,4-disubstituted, 1,2,4-trisubstituted and 1,2,4,5-tetra-substituted imidazoles via cascade palladium catalyzed C-C coupling followed by intramolecular C-N bond formation was developed. Readily accessible boronic acids and N-substituted-2-aminoacetonitriles were firstly reported as starting materials to construct di-, tri-, and tetra-substituted imidazoles in good to excellent yield.

1-Cyanoformamidines. Formation during the RuO4-mediated oxidation of secondary amines

When performed in the presence of cyanide and at pH smaller than 5, the RuO4-mediated oxidation of secondary amines Bn-NH-R (1a-b; R=Me, Et) gave mainly 1-cyanoformamidines Bn-NR-C(=NH)-CN (2a-b) and their hydrolysis products Bn-NR-COCN (3a-b), Bn-NR-CN (4a-b), Bn-NR-CONH2 (5a-b). Carboxamides 5a-b can result also directly from 1a-b. (Chemical Equation Presented).

AMINOPYRIMIDINYL COMPOUNDS

A compound having the structure: or a pharmaceutically acceptable salt thereof, wherein X is N or CR, where R is hydrogen, deuterium, C1-C4 alkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, aryl, heteroaryl, aryl(C1-C6 alkyl), CN, amino, alkylamino, dialkylamino, CF3, or hydroxyl; A is selected from the group consisting of a bond, C═O, —SO2—, —(C═O)NR0—, and —(CRaRb)q—, where R0 is H or C1-C4 alkyl, and Ra and Rb are independently hydrogen, deuterium, C1-C6 alkyl, C3-C6 cycloalkyl, aryl, aryl(C1-C6 alkyl), heteroaryl, (C1-C6 alkyl)heteroaryl, etc.; A′ is selected from the group consisting of a bond, C═O, —SO2—, —(C═O)NR0′, —NR0′(C═O)—, and —(CRa′Rb′)q—, where R0′ is H or C1-C4 alkyl, and Ra′ and Rb′ are independently hydrogen, deuterium, C1-C6 alkyl, C3-C6 cycloalkyl, aryl, aryl(C1-C6 alkyl), heteroaryl, (C1-C6 alkyl)heteroaryl, heteroaryl(C1-C6 alkyl), and heterocyclic(C1-C6 alkyl); Z is —(CH2)h— or a bond, where one or more methylene units are optionally substituted by one or more C1-C3 alkyl, CN, OH, methoxy, or halo, and where said alkyl may be substituted by one or more fluorine atoms; R1 and R1′ are independently selected from the group consisting of hydrogen, deuterium, C1-C4 alkyl, C3-C6 cycloalkyl, aryl, heteroaryl, aryl(C1-C6 alkyl), CN, etc., wherein said alkyl, aryl, cycloalkyl, heterocyclic, or heteroaryl is further optionally substituted with one or more substituents selected from the group consisting of C1-C6 alkyl, halo, CN, C1-C4 alkylamino, C3-C6 cycloalkyl, etc.; R2 is selected from the group consisting of hydrogen, deuterium, C1-C6 alkyl, C3-C6 cycloalkyl, halo, and cyano, where said alkyl may be substituted by one or more fluorine atoms; R3 is selected from the group consisting of hydrogen, deuterium, and amino; R4 is monocyclic or bicyclic aryl or monocyclic or bicyclic heteroaryl wherein said aryl or heteroaryl is optionally substituted with one or more substituents selected from the group consisting of C1-C6 alkyl, heterocycloalkyl, halo, C3-C6 cycloalkyl, etc., where said alkyl, cycloalkyl, alkoxy, or heterocycloalkyl may be substituted by one or more C1-C6 alkyl, halo, CN, OH, alkoxy, amino, —CO2H, —(CO)NH2, —(CO)NH(C1-C6 alkyl), or —(CO)N(C1-C6 alkyl)2, and where said alkyl may be further substituted by one or more fluorine atoms; R5 is independently selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6 alkoxy, and hydroxyl; h is 1, 2 or 3; j and k are independently 0, 1, 2, or 3; m and n are independently 0, 1 or 2; and, q is 0, 1 or 2. Also provided are methods of treatment as Janus Kinase inhibitors and pharmaceutical compositions containing the compounds of the invention and combinations with other therapeutic agents.