289686-74-4

Usage

Uses

Used in Chemical Synthesis:
2-Chloro-N-methoxy-N-methylbenzamide is used as a reagent in the synthesis of functionalized β-oxonitriles. These β-oxonitriles are important intermediates in the preparation of various organic compounds, including pharmaceuticals and agrochemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Chloro-N-methoxy-N-methylbenzamide is used in the synthesis of potent thiosemicarbazone-based cathepsin L inhibitors. Cathepsin L is a cysteine protease enzyme that plays a crucial role in various biological processes, including tumor progression and metastasis. Inhibitors of this enzyme have potential therapeutic applications in cancer treatment, as they can help regulate the activity of cathepsin L and prevent uncontrolled cell growth.

InChI:InChI=1/C9H10ClNO2/c1-11(13-2)9(12)7-5-3-4-6-8(7)10/h3-6H,1-2H3

Upstream product

• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 609-65-4 o-chlorobenzoyl chloride 
• 1117-97-1 N,0-dimethylhydroxylamine 
• 118-91-2 ortho-chlorobenzoic acid 
• 201230-82-2 carbon monoxide 
• 615-41-8 2-iodochlorobenzene 
• 17849-38-6 2-Chlorobenzyl alcohol 
• 98-88-4 benzoyl chloride 
• 6919-61-5 N-methoxy-N-methylbenzamide 
• 65-85-0 benzoic acid 

Downstream Products

• 91131-19-0 3-(dimethylamino)-1-(2-chlorophenyl)propan-1-one 
• 1385033-51-1 3-(2-chlorobenzoyl)benzonitrile 
• 89-98-5 2-chloro-benzaldehyde 
• 42330-59-6 (2-chloropyrid-3-yl)methanol 
• 3400-31-5 2-chloro-N-methylbenzamide 
• 24123-67-9 2,2‐dichloro‐1‐(2‐chlorophenyl)ethan‐1‐one 
• 34356-83-7 2,2‐dibromo‐1‐(2‐chlorophenyl)ethan‐1‐one 
• 348168-03-6 chloroisovalerophenone 
• 5162-03-8 (2-chlorophenyl)(phenyl)methanone 
• 79478-26-5 2-chloro-2-(2-chlorophenyl)-2-phenylacetaldehyde 
• 653-13-4 1-(2-chlorophenyl)-2,2-difluoroethanone 
• 40018-25-5 2-Chlorobenzoyl acetonitrile 
• 72867-72-2 1-(2-chlorophenyl)-2-phenyl-1-ethanone 

Relevant academic research and scientific papers

Flow Microreactor Technology for Taming Highly Reactive Chloroiodomethyllithium Carbenoid: Direct and Chemoselective Synthesis of α-Chloroaldehydes

A straightforward flow synthesis of α-chloro aldehydes has been developed. The strategy involves, for the first time, the thermal unstable chloroiodomethyllithium carbenoid and carbonyl compounds. A batch versus flow comparative study showcases the superb capability of flow technology in prolonging the lifetime of the lithiated carbenoid, even at -20 °C. Remarkably, the high chemoselectivity realized in flow allowed for preparing polyfunctionalized α-chloro aldehydes not easily accessible with traditional batch procedures.

Formation of Aryl [1-Cyano-4-(dialkylamino)butadienyl] Ketones from Pyridines

Treatment of 2-chloropyridine with LDA and the Weinreb amide of benzoic acid afforded three unusual products, namely N -methylbenzamide, 2-chloropyridine-3-methanol, and the ring-opened addition product. This same final product could also be obtained from 2-chloro-3-benzoylpyridine on treatment with LDA. Mechanistic insight for the formation of these products is provided.

Palladium-Catalyzed, ortho-Selective C-H Halogenation of Benzyl Nitriles, Aryl Weinreb Amides, and Anilides

A palladium-catalyzed, ortho-selective C-H halogenation methodology is reported herein. The highlight of the work is the highly selective C(sp2)-H functionalization of benzyl nitriles in the presence of activated C(sp3)-H bond, which results in good yields of the halogenated products with excellent regioselectivity. Along with benzyl nitriles, aryl Weinreb amides and anilides have been evaluated for the transformation using aprotic conditions. Mechanistic studies yield interesting aspects with respect to the pathway of the reaction and the directing group abilities.

Synthesis of Difluoromethyl Ketones from Weinreb Amides, and Tandem Addition/Cyclization of o-Alkynylaryl Weinreb Amides

[Difluoro(phenylsulfanyl)methyl]trimethylsilane (PhSCF2SiMe3) underwent a fluoride-induced nucleophilic addition to the carbonyl group of Weinreb amides to provide the corresponding difluoro(phenylsulfanyl)methyl ketones. These were

Copper-catalyzed synthesis of weinreb amides by oxidative amidation of alcohols

A simple and efficient protocol has been developed for the oxidative amidation of alcohols to Weinreb amides using tert-butyl hydroperoxide as an oxidant and an inexpensive and air stable copper catalyst. The present protocol is advantageous as it uses commercially affordable alcohols as starting materials. The developed protocol also tolerates various substituted alcohols as starting materials to provide good to excellent yields of the desired products.

Pd(OAc)2/DABCO as an efficient and phosphine-free catalytic system for the synthesis of single and double Weinreb amides by the aminocarbonylation of aryl iodides

This work reports a mild, stable and efficient Pd(OAc)2/DABCO catalysed protocol for the synthesis of single and double Weinreb amides. Double Weinreb amides, having 1,4-phenylene- and biphenylene-linkers-important backbones for the synthesis of biologically active symmetrical resorcylate oligomer units-were synthesized by the double carbonylation of aryl diiodides. Notably, the reaction does not require any expensive or air/moisture sensitive phosphine ligands. DABCO was found to be an inexpensive and stable ligand for the Pd(OAc)2 catalysed carbonylation of aryl iodides under an atmospheric pressure of carbon monoxide, and offered excellent yields of the single and double Weinreb amides. the Partner Organisations 2014.

Synthesis and structure-activity relationships of benzophenone-bearing diketopiperazine-type anti-microtubule agents

KPU-105 (4), a potent anti-microtubule agent that contains a benzophenone was derived from the diketopiperazine-type vascular disrupting agent (VDA) plinabulin 3, which displays colchicine-like tubulin depolymerization activity. To develop derivatives wit

ISOXAZOLE DERIVATIVES USED AS OESTROGEN MODULATORS

The present invention relates to a substituted isoxazole derivative according to formula (I), wherein the variables are defined as in the specification, or to a pharmaceutically acceptable salt, solvate or prodrug thereof. The present invention also relates to a pharmaceutical composition comprising said substituted isoxazole derivatives and to their use as a contraceptive or in therapy, for instance in the treatment or prevention of estrogen-receptor mediated disorders or estrogen-receptor related physiological conditions such as climacteric disorders and osteoporosis.

Synthesis and pharmacological evaluation of 3-aryl-3-azolylpropan-1-amines as selective triple serotonin/norepinephrine/dopamine reuptake inhibitors

A series of 3-aryl-3-azolylpropan-1-amines was prepared and screened for its capability of inhibiting monoamine reuptake. Analogs with nanomolar potency, good human in vitro microsomal stability, and low drug-drug interaction potential were described. In

Design, synthesis, and biological evaluation of potent thiosemicarbazone based cathepsin L inhibitors

A small library of 36 functionalized benzophenone thiosemicarbazone analogs has been prepared by chemical synthesis and evaluated for their ability to inhibit the cysteine proteases cathepsin L and cathepsin B. Inhibitors of cathepsins L and B have the potential to limit or arrest cancer metastasis. The six most active inhibitors of cathepsin L (IC50 50 > 10,000 nM). The most active analog in the series, 3-bromophenyl-2′-fluorophenyl thiosemicarbazone 1, also efficiently inhibits cell invasion of the DU-145 human prostate cancer cell line.