5892-99-9

Usage

Uses

Used in Pharmaceutical Research:
4-BROMO-N,N-DIETHYLBENZAMIDE is used as a key intermediate in the synthesis of SNC 80 (S590000), a highly selective and potent non-peptide delta-opioid receptor agonist. This makes it valuable for research and development of new drugs targeting the delta-opioid receptor, which has potential therapeutic applications in pain management and other conditions.
Used in Pain Management Research:
As a precursor to SNC 80, 4-BROMO-N,N-DIETHYLBENZAMIDE plays a crucial role in the development of novel pain management therapies. The delta-opioid receptor agonist SNC 80 has demonstrated high selectivity over other opioid receptors, which may lead to fewer side effects and a more targeted approach to pain relief.
Used in Drug Synthesis:
In the field of drug synthesis, 4-BROMO-N,N-DIETHYLBENZAMIDE is utilized as a building block for the creation of SNC 80 and potentially other related compounds. Its unique structure allows for the exploration of new chemical pathways and the development of innovative pharmaceutical agents.

InChI:InChI=1/C11H14BrNO/c1-3-13(4-2)11(14)9-5-7-10(12)8-6-9/h5-8H,3-4H2,1-2H3

Upstream product

• 109-89-7 diethylamine 
• 78823-39-9 C₁₂H₁₃BrO₃ 
• 617-84-5 N-formyldiethylamine 
• 873-75-6 4-bromobenzenemethanol 
• 201230-82-2 carbon monoxide 
• 5467-74-3 4-Bromophenylboronic acid 
• 589-87-7 1,4-bromoiodobenzene 
• 121-44-8 triethylamine 
• 586-76-5 4-Bromobenzoic acid 
• 16532-79-9 4-Bromophenylacetonitrile 
• 55441-26-4 2-(diethylamino)-2-oxoacetic acid 
• 374564-35-9 potassium 4-bromophenyltrifluoroborate 
• 586-75-4 4-chlorobenzoyl chloride 

Downstream Products

• 71888-24-9 4-(diethylaminocarbonyl)benzoic acid 
• 4885-19-2 1-(4-bromophenyl)-N,N-diethylmethanamine 
• 255850-50-1 p-(3-hydroxy-3-methyl-1-butynyl)-N,N-diethylbenzamide 
• 51207-85-3 4-amino-N,N-diethylbenzamide 
• 229479-39-4 N,N-Diethyl-4-[3-methoxyphenyl(1-propylpiperidin-4-yl)amino]benzamide Fumarate 
• 918811-37-7 4-Bromo-N,N-diethyl-2-formylbenzamide 
• 940532-00-3 N,N-diethyl-4-(3-phenylureido)benzamide 
• 79119-31-6 N, N-diethyl-4-hydroxybenzamide 
• 1615240-71-5 (E)-N,N-diethyl-2-(β-phenoxyvinyl)benzamide 
• 1615240-72-6 (Z)-N,N-diethyl-2-(β-phenoxyvinyl)benzamide 
• 1620210-46-9 N,N-diethyl-4-bromo-2-(1-phenylethyl)benzamide 

Relevant academic research and scientific papers

Pd-Catalyzed Oxidative Aminocarbonylation of Arylboronic Acids with Unreactive Tertiary Amines via C-N Bond Activation

An efficient synthesis of tertiary amides from aryl boronic acids and inert tertiary amines through the oxidative carbonylation via C(sp3)-N bond activation is presented. This protocol significantly restricts the homocoupling biarylketone product. It involves the use of a homogeneous PdCl2/CuI catalyst and a heterogeneous Pd/C based catalyst, which promotes C(sp3)-N bond activation of tertiary amines with aryl boronic acids. This process represents a ligand-free, base-free, and recyclable catalyst along with an ideal oxidant like molecular oxygen.

Palladium-Catalyzed N-Acylation of Tertiary Amines by Carboxylic Acids: A Method for the Synthesis of Amides

A palladium-catalyzed N-acylation of tertiary amines by carboxylic acids was achieved through C-N cleavage. This reaction showed a wide substrate scope. Both aromatic and aliphatic acids served well as the acylating reagents and coupled with tertiary amines to produce the corresponding amides in good to excellent yields. With the strategy, bioactive carboxylic acids were also efficiently modified, highlighting the synthetic value of the process in organic synthesis.

Clickable coupling of carboxylic acids and amines at room temperature mediated by SO2F2: A significant breakthrough for the construction of amides and peptide linkages

The construction of amide bonds and peptide linkages is one of the most fundamental transformations in all life processes and organic synthesis. The synthesis of structurally ubiquitous amide motifs is essential in the assembly of numerous important molecules such as peptides, proteins, alkaloids, pharmaceutical agents, polymers, ligands and agrochemicals. A method of SO2F2-mediated direct clickable coupling of carboxylic acids with amines was developed for the synthesis of a broad scope of amides in a simple, mild, highly efficient, robust and practical manner (>110 examples, >90% yields in most cases). The direct click reactions of acids and amines on a gram scale are also demonstrated using an extremely easy work-up and purification process of washing with 1 M aqueous HCl to provide the desired amides in greater than 99% purity and excellent yields.

Synthesis of Allylsilanes via Nickel-Catalyzed Cross-Coupling of Silicon Nucleophiles with Allyl Alcohols

NiCl2(PMe3)2-catalyzed reaction of allyl alcohols with silylzinc reagents, including PhMe2SiZnCl, Ph2MeSiZnCl, and Ph3SiZnCl, was performed, achieving allylsilanes in high yields. Aryl- and heteroaryl-substituted allyl alcohols, (E)-3-arylprop-2-en-1-ols, 1-aryl-prop-2-en-1-ols, and (E)-1-phenylpent-1-en-3-ol can be employed in the transformation. A range of functional groups as well as heteroaryl groups were tolerated. Reaction exhibited high regioselectivity and E/Z-selectivity when 1- or 3-aryl-substituted allyl alcohols were used as the substrates. Reaction of chiral allyl alcohol, (S,E)-1-phenylpent-1-en-3-ol, yielded a configuration-inversion product (R,E)-dimethyl(phenyl)(1-phenylpent-1-en-3-yl)silane.

NOVEL COMPOUND HAVING BLT INHIBITORY ACTIVITY AND COMPOSITION, FOR PREVENTING OR TREATING INFLAMMATORY DISEASES, COMPRISING SAME AS ACTIVE INGREDIENT

The present invention relates to a novel compound showing leukotriene B4 receptor 2 (BLT2) inhibitory activity and a pharmaceutical composition, for preventing or treating inflammatory diseases, comprising same as an active ingredient. The inventors identified a novel compound containing BTL2 inhibitory activity, and experimentally confirmed that the present novel compound had an excellent effect on the enhancement of the cancer cell death, on the inhibition of the metastasis and chemotactic mobility, and on the anti-asthma activity. Therefore, the present novel compound can be used as a very effective pharmaceutical component for treating the inflammatory-related diseases.

INHIBITORS OF LOW MOLECULAR WEIGHT PROTEIN TYROSINE PHOSPHATASE (LMPTP) AND USES THEREOF

Protein tyrosine phosphatases (PTPs) are key regulators of metabolism and insulin signaling. As a negative regulator of insulin signaling, the low molecular weight protein tyrosine phosphatase (LMPTP) is a target for insulin resistance and related conditions. Described herein are compounds capable of modulating the level of activity of low molecular weight protein tyrosine phosphatase (LMPTP) and compositions, and methods of using these compounds and compositions.

Versatile Heterogeneous Palladium Catalysts for Diverse Carbonylation Reactions under Atmospheric Carbon Monoxide Pressure

Herein, we report a versatile carbonylation protocol using heterogeneous Pd0 nanoparticles supported on the metal–organic frameworks (MOFs) MIL-88B-NH2 (Fe/Cr). The synthesis of a vast array of carbonyls, which includes amides, esters, carboxylic acids, and α-ketoamides, was achieved through mono- and dicarbonylation reactions. The selectivity could be controlled simply by tuning the reaction conditions. Superior activity and selectivity were recorded in some cases compared to that achieved with commercial Pd/C. However, the utility of an elaborate catalyst support is questionable and important reactivity and recyclability issues are discussed.

Direct Synthesis of Amides from Oxidative Coupling of Benzyl Alcohols and N-substituted Formamides Using a Co–Al Based Heterogeneous Catalyst

Present work reports the direct synthesis of amides from oxidative coupling of benzyl alcohols with various N-substituted formamides using a cobalt-hydrotalcite (Co-HT) derived catalyst. The Co-HT derived catalysts (Co-HT-2, Co-HT-3 and Co-HT-4 having Co2+/Al3+ molar ratio in the catalyst preparation mixture as 1/1, 2/1 and 3/1 respectively) were prepare following a co-precipitation method and characterized well by powder XRD, XPS, FEG-SEM, EDS, DTG–TGA, FT-IR and N2 physisorption measurements. A range of functional amides were obtained in good yields from oxidative coupling of various substituted benzyl alcohols and a range of N-substituted formamides using Co-HT-3 catalyst and oxidant TBHP. Mechanistic investigation suggests that the amidation reaction is associated with the formation and coupling of radical species. Furthermore, the Co-HT derived catalyst was easily recoverable and recyclable with retained high catalytic activity towards the oxidative coupling of benzyl alcohol with DMF. Graphical Abstract: [Figure not available: see fulltext.].

Palladium supported on triphenylphosphine-functionalized porous organic polymer: An efficient heterogeneous catalyst for aminocarbonylation

An efficient route for the catalytic synthesis of aryl amides via the aminocarbonylation of aryl iodides with amines is described using palladium supported on triphenylphosphine-functionalized porous organic polymer (Pd@KAPs(Ph-PPh3)) as the catalyst. Under low carbon monoxide pressure, the catalyst exhibited remarkable activity, and only 0.5 mol% palladium loading was required to achieve moderate to excellent yields (70-97 %) of aryl amides. The catalyst can be easily separated by a simple filtration process and recycled up to seven times with only minor loss of activity. The salient features of this protocol are the simplicity in handling of catalyst, low CO pressure, good functional group tolerance, high catalytic activity, negligible palladium leaching and effective catalyst recyclability.

Pd/C-catalyzed aminocarbonylation of aryl iodides via oxidative C-N bond activation of tertiary amines to tertiary amides

This work reports oxidative N-dealkylation/carbonylation of tertiary amines to tertiary amides by using molecular oxygen as a sole oxidant using a Pd/C catalyst. This protocol is free from ligands, additives, bases, and cocatalysts. Different tertiary amines as well as aryl iodides have been examined for this transformation, providing desired products in good to excellent yield.