135754-82-4

Usage

Uses

Used in Pharmaceutical Industry:
3,N-DIMETHYL-N-METHOXYBENZAMIDE is used as an intermediate in the synthesis of various pharmaceutical compounds for its ability to be modified and incorporated into more complex molecular structures. Its unique structural features make it a valuable building block for the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
3,N-DIMETHYL-N-METHOXYBENZAMIDE is used as a reactant in catalytic reactions for the synthesis of 4H-3,1-benzoxazin-4-ones. These benzoxazinones are important compounds with a wide range of applications, including their use as pharmaceuticals, agrochemicals, and dyes. The use of 3,N-DIMETHYL-N-METHOXYBENZAMIDE in this process highlights its versatility and utility in the synthesis of valuable chemical products.

InChI:InChI=1/C10H13NO2/c1-8-5-4-6-9(7-8)10(12)11(2)13-3/h4-7H,1-3H3

Upstream product

• 587-03-1 3-methylbenzyl alcohol 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 14040-11-0 tungsten hexacarbonyl 
• 591-17-3 meta-bromotoluene 
• 15226-74-1 dicobalt octacarbonyl 
• 13939-06-5 molybdenum hexacarbonyl 
• 1711-06-4 3-Methylbenzoyl chloride 
• 1117-97-1 N,0-dimethylhydroxylamine 
• 99-04-7 m-Toluic acid 

Downstream Products

• 844879-24-9 (3-bromophenyl)-m-tolylmethanone 
• 1394949-01-9 N,N-diethyl-3,5-dioxo-5-(m-tolyl)pentanamide 
• 54095-43-1 1-(3-methylphenyl)-3-phenylpropan-1-one 
• 1339733-17-3 2-hydroxy-N-methoxy-N,5-dimethylbenzamide 
• 1339570-02-3 2-hydroxy-N-methoxy-N,3-dimethylbenzamide 
• 620-23-5 m-tolyl aldehyde 
• 117039-85-7 6-methyl-2-phenyl-4H-benzo[d][1,3]oxazin-4-one 
• 95606-81-8 2-phenyl-1-(m-tolyl)ethan-1-one 
• 74786-81-5 m-methyl-N-methylbenzamide 
• 26954-33-6 1-(3-methylphenyl)pent-4-en-1-one 
• 1262282-36-9 2-iodo-N-methoxy-N,5-dimethylbenzamide 
• 50562-05-5 2,2-difluoro-1-(3-methylphenyl)ethan-1-one 
• 51772-30-6 3'-Methylpropiophenone 

Relevant academic research and scientific papers

Rhoda-Electrocatalyzed Bimetallic C?H Oxygenation by Weak O-Coordination

Rhodium-electrocatalyzed arene C?H oxygenation by weakly O-coordinating amides and ketones have been established by bimetallic electrocatalysis. Likewise, diverse dihydrooxazinones were selectively accessed by the judicious choice of current, enabling twofold C?H functionalization. Detailed mechanistic studies by experiment, mass spectroscopy and cyclovoltammetric analysis provided support for an unprecedented electrooxidation-induced C?H activation by a bimetallic rhodium catalysis manifold.

Iminyl Radicals by Reductive Cleavage of N-O Bond in Oxime Ether Promoted by SmI2: A Straightforward Synthesis of Five-Membered Cyclic Imines

A new generation method of N-centered radicals from the reductive cleavage of the N-O bond in oxime ether promoted by SmI2 is reported for the first time. The in-situ-generated N-centered radicals underwent intramolecular cyclization to afford five-membered cyclic imines in two manners: N-centered radical addition and N-centered anion nucleophilic substitution. From a synthetic point of view, an efficient synthetic method of five-membered cyclic imines was developed. A mechanism of the transformation was proposed.

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

Enantioselective Hydrogen Atom Transfer: Discovery of Catalytic Promiscuity in Flavin-Dependent 'Ene'-Reductases

Flavin has long been known to function as a single electron reductant in biological settings, but this reactivity has rarely been observed with flavoproteins used in organic synthesis. Here we describe the discovery of an enantioselective radical dehalogenation pathway for α-bromoesters using flavin-dependent 'ene'-reductases. Mechanistic experiments support the role of flavin hydroquinone as a single electron reductant, flavin semiquinone as the hydrogen atom source, and the enzyme as the source of chirality.

One-Pot Direct Synthesis of Weinreb Amides from Aryl and Hetero Aryl Halides Using Co 2(CO) 8 as an Effective CO Source under Conventional Thermal Heating

A successful protocol for the synthesis of Weinreb amides directly from aryl halides via aminocarbonylation with N,O-dimethyl hydroxylamine using Co2(CO)8 as an in situ CO source has been demonstrated. The effects of various reaction parameters such as temperature, base, and CO source have also been investigated and optimized. GRAPHICAL ABSTRACT.

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.

Ru-catalyzed hydrogenation of 3,5-diketo amides: Simultaneous control of chemo- and enantioselectivity

By modulating the chelating priorities of the different directing groups in 3,5-diketo amides with the assistance from coordinating solvent, highly chemo- and enantioselective hydrogenation of the C3-carbonyls was achieved in the presence of [RuCl(benzene)(S)-SunPhos]Cl in THF.

Scaffold hopping strategy toward original pyrazolines as selective CB 2 receptor ligands

In line of a scaffold hopping strategy of pyrazole structures, especially known as potent CB2 receptor antagonists, we exploited an original and convergent synthesis of a new class of C4-benzyl pyrazolines and derivatives from readily available

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.

Synthesis and Structure-Activity Relationship of Aminobenzophenones. A Novel Class of p38 MAP Kinase Inhibitors with High Antiinflammatory Activity

We wish to report the synthesis and structure-activity relationship (SAR) of a series of 4-aminobenzophenones, as a novel compound class with high antiinflammatory activity. Our initial lead, {4-[(2-aminophenyl)amino]phenyl}(phenyl)methanone (3), was systematically optimized and resulted in compounds that potently inhibited the release of the proinflammatory cytokines IL-1β and TNF-α in human peripheral blood mononuclear cells stimulated by LPS. One of the most potent compounds, among others, was {4-[(2-aminophenyl)amino]-2-chlorophenyl}(2-methylphenyl)methanone (45) with IC50 values of 14 and 6 nM for the inhibition of IL-1β and TNF-α, respectively. Furthermore, we found these types of compounds to be potent and selective p38 MAP kinase inhibitors, e.g. 45 had an IC50 value of 10 nM. Molecular modeling was used to rationalize our SAR data and to propose a model for the interaction of compound 45 with the p38 MAP kinase. The model involved a favorable hydrogen bond between the carbonyl group of the benzophenone and the NH of Met-109, positioning ring A in the hydrophobic pocket I of the enzyme. Good antiinflammatory effects were demonstrated in two murine models of dermatitis after topical application (oxazolone and TPA model).