89302-15-8

Usage

Uses

Used in Pharmaceutical Industry:
(5-METHOXY-2-NITRO-PHENYL)-ACETONITRILE is used as a reagent and intermediate for the synthesis of various drugs and active pharmaceutical ingredients. Its unique structure, which includes a phenyl ring with functional groups, makes it a valuable component in the creation of new compounds with potential therapeutic effects.
Used in Organic Synthesis:
In the realm of organic synthesis, (5-METHOXY-2-NITRO-PHENYL)-ACETONITRILE is utilized as a key intermediate. Its presence of both electron-donating and electron-withdrawing groups allows for a wide range of chemical reactions, facilitating the development of diverse chemical entities with specific applications in various fields.

InChI:InChI=1/C9H8N2O3/c1-14-8-2-3-9(11(12)13)7(6-8)4-5-10/h2-3,6H,4H2,1H3

Upstream product

• 100-17-4 para-methoxynitrobenzene 
• 3598-13-8 (4-chlorophenoxy)acetonitrile 
• 97655-38-4 ethyl α-cyano-5-methoxy-2-nitrobenzene acetate 
• 19924-43-7 3-methoxyphenylacetonitrile 
• 5367-32-8 5-methoxy-2-nitrotoluene 
• 67567-46-8 2‐(bromomethyl)‐4‐methoxy‐1‐nitrobenzene 
• 100-02-7 4-nitro-phenol 
• 82204-34-0 (5-methoxy-2-nitro-phenyl)-pyruvic acid 
• 28987-59-9 3-chloro-4-nitroanisole 
• 40140-91-8 3-chloro-4-nitrosophenol 
• 491-11-2 3-chloro-4-nitrophenol 
• 61540-35-0 S-(Dimethylthiocarbamoyl)thioglycolonitrile 

Downstream Products

• 857226-30-3 2-(5-methoxy-2-nitro-phenyl)-3-(3,4,5-trimethoxy-phenyl)-propionitrile 
• 1006-94-6 5-methoxylindole 
• 138469-69-9 2-(5-methoxy-2-nitrophenyl)pent-4-enenitrile 
• 138469-73-5 2-cyclohexyl-2-(2-nitro-5-methoxyphenyl)acetonitrile 
• 21857-41-0 methyl 2-(5-methyl-2-nitrophenyl)acetate 
• 20876-29-3 2-(5-methoxy-2-nitrophenyl)acetic acid 
• 1310481-72-1 2-(5-methoxy-2-nitrophenyl)-3-phenyl-2-pentenenitrile 
• 1310481-73-2 3-cyano-2-(1-phenylethyl)-5-methoxyindole 
• 481668-37-5 5-methoxy-2-methyl-1H-indole-3-carbonitrile 
• 1159006-91-3 6-[4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-pyrimidine-4-carboxylic acid benzyl-(2,2,2-trifluorethyl)-amide 
• 1159006-95-7 7-methoxy-3-{1-[6-(3-phenyl-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one 
• 1159007-53-0 6-[4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-pyrimidine-4-carboxylic acid-phenylamide 
• 111795-98-3 ethyl-4-cyano-4-(5-methoxy-2-nitrophenyl)butyrate 
• 90557-38-3 (2-amino-5-methoxyphenyl)-acetonitrile 

Relevant academic research and scientific papers

Palladium-Catalyzed Dual Annulation: A Method for the Synthesis of Norneocryptolepine

A novel procedure for the Pd-catalyzed dual annulation reaction to synthesize the norneocryptolepine derivatives involving the concerted construction of two central heterocycles is reported. The further methylation of the norneocryptolepine to afford its alkaloid analog neocryptolepine implies that synthesis of various neocryptolepine derivatives is feasible. The oxidative addition of Pd(0) is indicated as the key step to activate the intramolecular addition of nitrile according to the mechanism study.

NOVEL HETEROCYCLIC COMPOUNDS AND USE THEREOF IN MEDICINE AND IN COSMETICS

The invention relates to novel heterocyclic compounds of general formula (I), as well as their pharmaceutically acceptable salts, and their enantiomers. The invention also relates to the use thereof as a medicinal product, preferably in the prevention and/or treatment of inflammatory diseases with a neurogenic component or use thereof as a cosmetic. The compounds of the present invention act as antagonists of the CGRP-R receptor.

Active and Recyclable Catalytic Synthesis of Indoles by Reductive Cyclization of 2-(2-Nitroaryl)acetonitriles in the Presence of Co-Rh Heterobimetallic Nanoparticles with Atmospheric Hydrogen under Mild Conditions

A cobalt-rhodium heterobimetallic nanoparticle-catalyzed reductive cyclization of 2-(2-nitroaryl)acetonitriles to indoles has been achieved. The tandem reaction proceeds without any additives under the mild conditions (1 atm H2 and 25 °C). This procedure could be scaled up to the gram scale. The catalytic system is significantly stable under these reaction conditions and could be reused more than ten times without loss of catalytic activity.

Novel synthesis of benzofuran- and indol-2-yl-methanamine derivatives

We report on a novel synthesis towards benzofuran-2-yl-methanamine and indol-2-yl-methanamine derivatives by using ortho-methoxy and ortho-nitro substituted phenylacetic acids as starting material, respectively. For each compound series, a key intermediate bearing the oxazole-4-carboxylic acid methylester moiety was produced. Refluxing the ortho-methoxy series in HBr/HAc produced the desired benzofuran-2-yl-methanamines. Accordingly, for the synthesis of indoles the nitro-group was first reduced and refluxing these intermediates in HCl gave the corresponding indol-2-yl-methanamines. The method worked well with electron donating substituents. Limitations regarding electron withdrawing substituents are discussed. This straightforward synthetic procedure can be a useful approach to generate a variety of substituted benzofuran-2-yl-methanamine and indol-2-yl-methanamine compounds by starting from readily available phenylacetic acid derivatives.

CGRP ANTAGONISTS

The present invention relates to new CGRP-antagonists of general formula I wherein U, V, X, Y, R1, R2 and R3 are defined as stated hereinafter, the tautomers, the isomers, the diastereomers, the enantiomers, the hydrates, the mixtures thereof and the salts thereof and the hydrates of the salts, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, pharmaceutical compositions containing these compounds, their use and processes for preparing them.

NOVEL COMPOUNDS

The present invention relates to new CGRP-antagonists of general formula I wherein U, V, X, Y, R1, R2, R3 and R4 are defined as mentioned in the description, the tautomers thereof, the isomers thereof, the diastereomers thereof, the enantiomers thereof, the hydrates thereof, the mixtures thereof and the salts thereof as well as the hydrates of the salts, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, medicaments containing these compounds, the use thereof and processes for the preparation thereof.

Synthesis, structure-activity relationship and crystallographic studies of 3-substituted indolin-2-one RET inhibitors

The synthesis, structure-activity relationships (SAR) and structural data of a series of indolin-2-one inhibitors of RET tyrosine kinase are described. These compounds were designed to explore the available space around the indolinone scaffold within RET active site. Several substitutions at different positions were tested and biochemical data were used to draw a molecular model of steric and electrostatic interactions, which can be applied to design more potent and selective RET inhibitors. The crystal structures of RET kinase domain in complex with three inhibitors were solved. All three compounds bound in the ATP pocket and formed two hydrogen bonds with the kinase hinge region. Crystallographic analysis confirmed predictions from molecular modelling and helped refine SAR results. These data provide important information for the development of indolinone inhibitors for the treatment of RET-driven cancers.

NOVEL COMPOUNDS

The present invention relates to new CGRP-antagonists of general formulae Ia and Ib wherein R1, R2, R3, R4 and R5 are defined as mentioned below, the tautomers, the isomers, the diastereomers, the enantiomers, the hydrates, the mixtures and the salts thereof as well as the hydrates of the salts, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, pharmaceutical compositions containing these compounds, the use thereof and processes for the preparation thereof.

Short and simple method of synthesis of some pyrrolo[3,2-b]quinoline derivatives from easily available nitrobenzene derivatives

The Vilsmeier-Hack condensation of ortho-cyanomethylated nitroarenes with N-methylpyrrolidone, followed by cyclization promoted by O,N- bistrimethylsilylacetamide and DBU in DMF led directly to pyrrolo[3,2-b] quinoline derivatives. Georg Thieme Verlag Stuttgart · New York.

Azomethine ylide cycloaddition/reductive heterocyclization approach to oxindole alkaloids: Asymmetric synthesis of (-)-horsfiline

The intermolecular [3 + 2] with 2(2-nitrophenyl)acrylate dienophiles followed by reductive heterocyclization affords the spiro(indole-pyrrolidine) ring system. Hence, this enable us to accomplish a concise and highly enantioselective synthesis of (-)-horsfiline 1, based on chiral auxiliary-directed π-face discrimination in the 1,3-dipolar cycloaddition of (1S,2R)- 2-phenyl-1-cyclohexyl ester 4f with N-methylazomethine ylide.