214971-18-3

Usage

Uses

Used in Pharmaceutical Industry:
Benzamide, 2-amino-4-chloro-N-methoxy-N-methylis used as a building block for the synthesis of various drugs and biologically active molecules. Its unique structure allows for the development of new compounds with potential therapeutic applications.
Used in Therapeutic Applications:
Benzamide, 2-amino-4-chloro-N-methoxy-N-methylhas been studied for its potential therapeutic applications, including as an antipsychotic and an anti-inflammatory agent. Its unique chemical properties make it a promising candidate for the development of new treatments for various conditions.
Used in Cancer Treatment Research:
Additionally, 2-amino-4-chloro-N-methoxy-N-methyl-benzamide has been investigated for its role in the treatment of cancer and other diseases. Its potential as a therapeutic agent is currently being explored in ongoing research.

Upstream product

• 40928-13-0 4-chloroisatoic anhydride 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 89-77-0 2-Amino-4-chlorobenzoic acid 

Downstream Products

• 4076-50-0 2-amino-4-chlorobenzophenone 
• 223247-80-1 (2-Amino-4-chlorophenyl)-(3-methoxyphenyl)-methanone 
• 97296-01-0 N-(2-benzoyl-5-chlorophenyl)-4-methylbenzenesulfonamide 

Relevant academic research and scientific papers

Iridium-Catalyzed C-H Amination of Weinreb Amides: A Facile Pathway toward Anilines and Quinazolin-2,4-diones

C-H amination of arenes directed by weakly coordinating Weinreb amides has been achieved with an iridium catalyst and 2,2,2-trichloroethoxycarbonyl (Troc) azide as an aminating agent, providing a robust method of producing synthetic useful ortho-TrocNH aryl Weinreb amides. Taking advantage of the reactivity of Weinreb amide and Troc groups in the amination products, selective hydrolysis was achieved as an attractive process for the synthesis of ortho-NH2 aryl Weinreb amides, which are the building blocks useful in the synthesis of bioactive compounds, and cascade aminocyclization with primary amines was successful and provided an efficient pathway for the construction of quinazolin-2,4-diones, which are present in various alkaloids and natural products.

One-Pot Synthesis of Spirocyclopenta[ a]indene Derivatives via a Cascade Ring Expansion and Intramolecular Friedel-Crafts-Type Cyclization

A one-pot efficient synthetic approach for the rapid construction of spirocyclopenta[a]indene derivatives has been developed via an iodine-initiated cascade ring expansion and intramolecular Friedel-Crafts-type cyclization from propargyl alcohol-tethered alkylidenecyclobutanes under mild conditions with broad substrate scope. This cascade process can be elegantly conducted on a gram scale. A plausible reaction mechanism has been proposed on the basis of a series of deuterium labeling and control experiments.

Visible Light Induced Cyclization to Spirobi[indene] Skeletons from Functionalized Alkylidienecyclopropanes

In this paper, we revealed a metal-free and visible light photoinduced method for the rapid construction of spirobi[indene] skeletons, providing a simple and efficient way for easy access to spirobi[indene] scaffolds under mild conditions along with a broad substrate scope and good functional group tolerance.

Organocatalytic Atroposelective Friedl?nder Quinoline Heteroannulation

An atroposelective Friedl?nder heteroannulation reaction of 2-aminoaryl ketones with α-methylene carbonyl derivatives has been developed for the first time with chiral phosphoric acid as an efficient organocatalyst. The desired enantioenriched axially chi

Synthesis of Diiodinated All-Carbon 3,3′-Diphenyl-1,1′-spirobiindene Derivatives via Cascade Enyne Cyclization and Electrophilic Aromatic Substitution

A synthetic method for the construction of diiodinated all-carbon spirobiindene derivatives has been developed from the reaction of propargyl alcohol-tethered alkylidenecyclopropanes with iodine. The reaction proceeded through an iodination-initiated cascade intramolecular enyne cyclization and electrophilic aromatic substitution reaction process in 1,2-dichloroethane upon heating, giving desired spirocyclic products in moderate to excellent yields. Further transformation of the obtained products has also been presented.

Palladium-Catalyzed Cascade Reductive and Carbonylative Cyclization of Ortho-Iodo-Tethered Methylenecyclopropanes (MCPs) Using N-Formylsaccharin as CO Source

A palladium-catalyzed reductive and carbonylative cyclization of ortho-iodo-tethered methylenecyclopropanes (MCPs) using N-formylsaccharin as CO source has been developed, affording the desired indanone derivatives in moderate to good yields with high regio- and stereoselectivity and good functional group compatibility.

Catalytic Asymmetric Synthesis of Atropisomeric Quinolines through the Friedl?nder Reaction

A phosphoric acid catalyzed atroposelective Friedl?nder reaction was developed in which acetylacetone and a variety of 2′-substituted 2-Aminobenzophenones were successfully employed to give optically active biaryl quinolines in good yields and with high enantioselectivities.

Gram-Positive and Gram-Negative Antibiotic Activity of Asymmetric and Monomeric Robenidine Analogues

Desymmetrisation of robenidine (1: N′,2-bis((E)-4-chlorobenzylidene)hydrazine-1-carboximidhydrazide) and the introduction of imine alkyl substituents gave good antibiotic activity. Of note was the increased potency of two analogues against vancomycin-resistant Enterococci (VRE), one of which returned a MIC of 0.5 μg mL?1. Five analogues were found to be equipotent or more potent than the lead 1. Introduction of an indole moiety resulted in the most active robenidine analogue against methicillin-resistant S. aureus (MRSA), with a MIC of 1.0 μg mL?1. Imine C=NH isosteres (C=O/C=S) were inactive. Monomeric analogues were 16–64 μg mL?1 active against MRSA and VRE. An analogue that lacks the terminal hydrazide NH moiety showed modest Gram-negative activity at 64 μg mL?1. A 4-tert-butyl analogue was shown to be active against both Gram-positive and -negative strains at 16–64 μg mL?1. In general, additional modifications with aromatic moieties was poorly tolerated, except with concomitant introduction of an imine C-alkyl group. The activity of these analogues against MRSA and VRE ranged from 8 μg mL?1 to inactive (MIC>128 μg mL?1) with the naphthyl and indole analogues. Gram-negative activity was most promising with two compounds at 16 μg mL?1 against E. coli. Against P. aeruginosa, the highest activity observed was with MIC values of 32 μg mL?1 with another two analogues. Combined, these findings support the further development of the (E)-2-benzylidenehydrazine-1-carboximidamide scaffold as a promising scaffold for the development of antibiotics against Gram-positive and Gram-negative strains.

Cascade Amination/Cyclization/Aromatization Process for the Rapid Construction of [2,3-c]Dihydrocarbazoles and [2,3-c]Carbazoles

An intramolecular cascade amination/cyclization/aromatization reaction of functionalized alkylidenecyclopropanes has been developed in the presence of silver acetate, affording a variety of [2,3-c]dihydrocarbazoles and [2,3-c]carbazoles in moderate to excellent yields. The mechanistic investigations revealed that this cascade reaction proceeds through a radical initiated process. Moreover, further transformations for the synthesis of eustifoline-D and an OLED exhibit a potential synthetic utility of this method.

Quinazoline derivatives, process for their preparation, their use as antimitotics and pharmaceutical compositions comprising said derivatives

The invention relates to quinazoline derivatives of formula (I) in which R1, X and A have the meanings as indicated, or to a pharmaceutically acceptable salt thereof, e.g. Such compounds are useful as modulators, in particular inhibitors, of th