155586-39-3

Usage

Uses

Used in Pharmaceutical Industry:
N,3,5-Trimethoxy-N-methylbenzamide is used as a pharmaceutical intermediate for its ability to facilitate the synthesis of various medications. Its role in the production process is vital, as it contributes to the development of new and effective drugs.
Used in Antitumor Agent Synthesis:
In the field of oncology, N,3,5-Trimethoxy-N-methylbenzamide is utilized as a key component in the synthesis of potential antitumor agents. Its chemical properties make it suitable for creating compounds that can target and combat cancer cells, offering hope for the development of novel and more effective cancer treatments.
Used in Organic Synthesis:
Beyond its pharmaceutical applications, N,3,5-Trimethoxy-N-methylbenzamide also serves as an intermediate in the synthesis of other organic compounds and materials. Its versatility in chemical reactions allows it to be a valuable component in a wide range of organic synthesis processes, contributing to the creation of various products across different industries.

InChI:InChI=1/C11H15NO4/c1-12(16-4)11(13)8-5-9(14-2)7-10(6-8)15-3/h5-7H,1-4H3

Upstream product

• 2150-37-0 methyl 3,5-dimethoxybenzoate 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 17213-57-9 3,5-dimethoxybenzoyl chloride 
• 1132-21-4 3,5-dimethoxybenzoic acid 
• 20469-65-2 1-bromo-3,5-dimethoxybenzene 
• 82102-37-2 9-methyl-9H-fluorene-9-carbonyl chloride 

Downstream Products

• 197587-19-2 1-(3,5-dimethoxyphenyl)-7-phenoxyheptan-1-one 
• 39192-51-3 1-(3,5-dimethoxyphenyl)heptan-1-one 
• 197587-20-5 3,5-dimethoxy-1-(2-methyl-8-phenoxyoctan-2-yl)benzene 
• 492447-05-9 1-[4-(7-bromo-1,1-dimethylheptyl)-2,6-dihydroxyphenyl]ethan-1-one 
• 492447-07-1 1-[2-allyloxy-4-(7-bromo-1,1-dimethylheptyl)-6-hydroxyphenyl]ethanone 
• 492447-03-7 1-[4-(1,1-dimethyl-7-phenoxyheptyl)-2,6-dimethoxyphenyl]ethan-1-one 
• 492447-10-6 1-[2-allyloxy-4-(7-bromo-1,1-dimethyl-heptyl)-6-hydroxy-phenyl]-10-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-7-methyl-dec-6-en-8-yn-1-one 
• 492447-12-8 1-[2-allyloxy-4-(7-bromo-1,1-dimethyl-heptyl)-6-hydroxy-phenyl]-10-(tert-butyl-dimethyl-silanyloxy)-7-methyl-dec-6-en-8-yne-1,3-diol 
• 60526-81-0 1-(1',1'-dimethylheptyl)-3,5-dimethoxybenzene 
• 303113-15-7 1-[4-(1,1-dimethylheptyl)-2,6-dimethoxyphenyl]ethan-1-one 
• 303113-16-8 1-[4-(1,1-dimethylheptyl)-2-hydroxy-6-prop-2-enyloxyphenyl]ethan-1-one 
• 303113-17-9 (6E)-1-[4-(1,1-dimethylheptyl)-2-hydroxy-6-prop-2-enyloxyphenyl]-3-hydroxy-10-tert-butyldimethylsilyloxy-7-methyldec-6-en-8-yn-1-one 
• 303113-18-0 (6E)-1-[4-(1,1-dimethylheptyl)-2-hydroxy-6-prop-2-enyloxyphenyl]-10-tert-butyldimethylsilyloxy-7-methyldec-6-en-8-yne-1,3-diol 
• 160512-71-0 5-(8-bromo-2-methyloctan-2-yl)benzene-1,3-diol 

Relevant academic research and scientific papers

Access to Aryl and Heteroaryl Trifluoromethyl Ketones from Aryl Bromides and Fluorosulfates with Stoichiometric CO

We report a sequential one-pot preparation of aromatic trifluoromethyl ketones starting from readily accessible aryl bromides and fluorosulfates, the latter easily prepared from the corresponding phenols. The methodology utilizes low pressure carbon monoxide generated ex situ from COgen to generate Weinreb amides as reactive intermediates that undergo monotrifluoromethylation affording the corresponding aromatic trifluoromethyl ketones (TFMKs) in good yields. The stoichiometric use of CO enables the possibility for accessing 13C-isotopically labeled TFMK by switching to the use of 13COgen.

Synthesis of various acylating agents directly from carboxylic acids

A straightforward synthesis of acylating reagents such as Weinreb and MAP amides from aromatic, aliphatic carboxylic acids, and amino acids using PPh3/NBS combination is described. A chemo-selective modification of the carboxylic acid group into Weinreb amide in the presence of more reactive aldehydes and ketones is presented. All reactions were performed at ambient temperature under air using undried commercial grade solvent. Furthermore, the present methodology could be performed at a gram scale under inert-free reaction conditions. In addition, 7-azaindoline amide auxiliary (used for catalytic asymmetric aldol- and Mannich-type reactions), which behaves like Weinreb amide is also synthesized under similar reaction conditions.

Synthesis, radio-synthesis and in vitro evaluation of terminally fluorinated derivatives of HU-210 and HU-211 as novel candidate PET tracers

We report the synthesis of terminally fluorinated HU-210 and HU-211 analogues (HU-210F and HU-211F, respectively) and their biological evaluation as ligands of cannabinoid receptors (CB1 and CB2) and N-methyl d-aspartate receptor (NMDAR). [18F]-labelled HU-210F was radiosynthesised from the bromo-substituted precursor. In vitro assays showed that both HU-210F and HU-211F retain the potent pharmacological profile of HU-210 and HU-211, suggesting that [18F]-radiolabelled HU-210F and HU-211F could have potential as PET tracers for in vivo imaging.

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

PROCESS FOR THE PRODUCTION OF CANNABIDIOL AND DELTA-9-TETRAHYDROCANNABINOL

The present disclosure relates to the preparation of a cannabidiol compound or a derivative thereof. The cannabidiol compound or derivatives thereof can be prepared by an acid-catalyzed reaction of a suitably selected and substituted di-halo-olivetol or derivative thereof with a suitably selected and substituted cyclic alkene to produce a dihalo-cannabidiol compound or derivative thereof. The dihalo-cannabidiol compound or derivative thereof can be produced in high yield, high stereospecificity, or both. It can then be converted under reducing conditions to a cannabidiol compound or derivatives thereof.

A Weinreb amide approach to the synthesis of trifluoromethylketones

A novel route to access trifluoromethylketones (TFMKs) from Weinreb amides is reported. This represents the first documented case of the Ruppert-Prakash reagent (TMS-CF3) reacting in a constructive manner with an amide and enables synthesis of TMFKs without risk of over-trifluoromethylation.

BENZOPHENONES AS INHIBITORS OF REVERSE TRANSCRIPTASE

The present invention includes benzophenone compounds (I) which are useful in the treatment of HIV infections.

Structure-activity relationship studies of novel benzophenones leading to the discovery of a potent, next generation HIV nonnucleoside reverse transcriptase inhibitor

Despite the progress of the past two decades, there is still considerable need for safe, efficacious drugs that target human immunodeficiency virus (HIV). This is particularly true for the growing number of patients infected with virus resistant to currently approved HIV drugs. Our high throughput screening effort identified a benzophenone template as a potential nonnucleoside reverse transcriptase inhibitor (NNRTI). This manuscript describes our extensive exploration of the benzophenone structure-activity relationships, which culminated in the identification of several compounds with very potent inhibition of both wild type and clinically relevant NNRTI-resistant mutant strains of HIV. These potent inhibitors include 70h (GW678248), which has in vitro antiviral assay IC50 values of 0.5 nM against wild-type HIV, 1 nM against the K103N mutant associated with clinical resistance to efavirenz, and 0.7 nM against the Y181C mutant associated with clinical resistance to nevirapine. Compound 70h has also demonstrated relatively low clearance in intravenous pharmacokinetic studies in three species, and it is the active component of a drug candidate which has progressed to phase 2 clinical studies.

Synthesis of functionalized cannabinoids

An effective synthesis of tricyclic, nonclassical cannabinoids has been developed on the basis of a cation-olefin cyclization that forms the two nonaromatic rings with the desired stereochemistry in a single step.

A new general method for preparation of N-methoxy-N-methylamides. Application in direct conversion of an ester to a ketone

The reaction of an ester with N,O-dimethylhydroxylamine and a suitable organomagnesium reagent or lithium amide base provides a general method for the preparation of N-methoxy-N-methylamides. Application in the direct conversion of a highly hindered ester to a ketone, the azasteroid 5α-reductase inhibitor MK-0434, is described.