25216-74-4

Usage

Uses

Used in Chemical Synthesis:
N-(TERT-BUTOXYCARBONYL)-3-BROMOANILINE is used as a protected amine in chemical synthesis for the purpose of preventing unwanted reactions at the amine group. This protection is particularly useful when the amine group needs to be preserved for subsequent reactions or when it is necessary to avoid interference with other functional groups present in the molecule.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-(TERT-BUTOXYCARBONYL)-3-BROMOANILINE is used as an intermediate in the synthesis of various drugs and active pharmaceutical ingredients. The protection of the amine group allows for the creation of complex molecular structures with precise control over the reactivity of different functional groups, leading to the development of more effective and targeted medications.
Used in Material Science:
N-(TERT-BUTOXYCARBONYL)-3-BROMOANILINE can also be utilized in the field of material science, particularly in the development of novel polymers and materials with specific properties. The protected amine group can be strategically incorporated into the molecular structure to influence the material's characteristics, such as its reactivity, stability, or mechanical properties.

InChI:InChI=1/C11H14BrNO2/c1-11(2,3)15-10(14)13-9-6-4-5-8(12)7-9/h4-7H,1-3H3,(H,13,14)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 591-19-5 m-Bromoaniline 
• 34619-03-9 tert-butyldicarbonate 
• 110-05-4 di-tert-butyl peroxide 
• 148854-09-5 1-bromo-3-isocyanobenzene 
• 111331-82-9 3-[(tert-butoxycarbonyl)amino]benzoic acid 
• 108-86-1 bromobenzene 
• 4248-19-5 tert-butyl carbazate 

Downstream Products

• 883199-27-7 N-[3-(2-chloropyrimidin-4-yl)-phenyl]-carbamic acid 1,1-dimethylethyl ester 
• 214961-34-9 2-amino-3'-tert-butoxycarbonylamino-5-chlorobenzophenone 
• 330793-09-4 tert-butyl N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl]carbamate 
• 1257310-85-2 [3-(2-trimethylsilanylethoxycarbonylamino)phenyl]carbamic acid tert-butyl ester 
• 1450821-90-5 tert-butyl 3-bromophenyl(4,6-dichloropyrimidin-2-yl)carbamate 
• 66584-32-5 3-bromo-N-methylaniline 
• 869090-19-7 methyl (S)-2-benzyloxy-3-[3'-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoate 
• 869090-08-4 N-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 
• 869089-98-5 tert-butyl {4'-[3-(4(S)-benzyl-2-oxo-oxazolidin-3-yl)-2(S)ethoxy-1(R)-hydroxy-3-oxopropyl]-biphenyl-3-yl}methylcarbamate 

Relevant academic research and scientific papers

A Unified Approach to Decarboxylative Halogenation of (Hetero)aryl Carboxylic Acids

Aryl halides are a fundamental motif in synthetic chemistry, playing a critical role in metal-mediated cross-coupling reactions and serving as important scaffolds in drug discovery. Although thermal decarboxylative functionalization of aryl carboxylic acids has been extensively explored, the scope of existing halodecarboxylation methods remains limited, and there currently exists no unified strategy that provides access to any type of aryl halide from an aryl carboxylic acid precursor. Herein, we report a general catalytic method for direct decarboxylative halogenation of (hetero)aryl carboxylic acids via ligand-to-metal charge transfer. This strategy accommodates an exceptionally broad scope of substrates. We leverage an aryl radical intermediate toward divergent functionalization pathways: (1) atom transfer to access bromo- or iodo(hetero)arenes or (2) radical capture by copper and subsequent reductive elimination to generate chloro- or fluoro(hetero)arenes. The proposed ligand-to-metal charge transfer mechanism is supported through an array of spectroscopic studies.

MYST FAMILY HISTONE ACETYLTRANSFERASE INHIBITORS

The present disclosure provides compounds, pharmaceutically acceptable compositions thereof, and methods of using the same.

Complexes featuring N-heterocyclic carbenes with bowl-shaped wingtips

Three imidazolium salts having their two N-substituents equipped with remote calix[4]arenyl termini have been synthesised and converted into N-heterocyclic carbene (NHC) complexes of the type [PdCl2(NHC)(pyridine)]. An X-ray diffraction study c

FNEW ACTIVATORS OF SIRT1 ENZYME FOR THE TREATMENT OF CARDIOVASCULAR AND CARDIOMETABOLIC PATHOLOGIES

This invention describes a class of compounds able to activate the human SIRT1 enzyme and regulate many metabolic functions. This invention relates to compounds that can be employed in medical applications, specifically for the treatment or prevention of cardiometabolic diseases, such as diabetes, and of cardiovascular disorders, such as coronaropathy, heart failure and atherosclerosis.

Investigation of the molecular characteristics of bisindole inhibitors as HIV-1 glycoprotein-41 fusion inhibitors

In previous work, we described 6-6‘-bisindole compounds targeting a hydrophobic pocket on the N-heptad repeat region of viral glycoprotein-41 as effective inhibitors of HIV-1 fusion. Two promising compounds with sub-micromolar IC50's contained a benzoic acid group and a benzoic acid ester attached at the two indole nitrogens. Here we have conducted a thorough structure-activity relationship (SAR) study evaluating the contribution of each of the ring systems and various substituents to compound potency. Hydrophobicity, polarity and charge were varied to produce 35 new compounds that were evaluated in binding, cell-cell fusion and viral infectivity assays. We found that (a) activity based solely on increasing hydrophobic content plateaued at ～ 200 nM; (b) the bisindole scaffold surpassed other heterocyclic ring systems in efficacy; (c) a polar interaction possibly involving Gln575 in the pocket could supplant less specific hydrophobic interactions; and (d) the benzoic acid ester moiety did not appear to form specific contacts with the pocket. The importance of this hydrophobic group to compound potency suggests a mechanism whereby it might interact with a tertiary component during fusion, such as membrane. A promising small molecule 10b with sub-μM activity was discovered with molecular weight 500 da and reduced logP compared to earlier compounds. The work provides insight into requirements for small molecule inhibition of HIV-1 fusion.

Effective approach to ureas through organocatalyzed one-pot process

An efficient approach to N, N′-unsymmetrically substituted ureas 9 has been developed through the ammonolysis process of N-Boc protected anilines 7 with amines prompted by 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD). Moreover, a convenient protocol for the

Selective Oxidative Coupling Reaction of Isocyanides Using Peroxide as Switchable Alkylating and Alkoxylating Reagent

A switchable oxidative coupling reaction of isocyanide and peroxide has been disclosed. In the presence of iron catalyst, the coupling reaction affords N-arylacetamides in good yields. By simply replacing the iron with copper catalyst, another different coupling reaction takes place in which peroxide can serve as alkoxylating source. This protocol represents a new fundamental coupling of two basic chemicals involving C?C and C?O bond-forming process. The unusual reactivity of an isocyano group in a radical reaction acting formally as an amidoyl synthon has also been well established. The experiment outcome reveals that aromatic isocyanides are particularly compatible reaction partners in present coupling reaction, whereas no desired products are observed when aliphatic isocyanides are used. (Figure presented.).

A relay FRET event in a designed trichromophoric pentapeptide containing an: O -, m -aromatic-amino acid scaffold

The concept of a relay FRET event is established in a designed trichromophoric pentapeptide containing an o-,m-aromatic amino acid scaffold in the backbone as a novel β-turn mimetic β-sheet folding nucleator. This system would find application in studying fundamental processes involving interbiomolecular interactions in chemical biology.

Reevaluating the Substrate Specificity of the L-Type Amino Acid Transporter (LAT1)

The L-type amino acid transporter 1 (LAT1, SLC7A5) transports essential amino acids across the blood-brain barrier (BBB) and into cancer cells. To utilize LAT1 for drug delivery, potent amino acid promoieties are desired, as prodrugs must compete with millimolar concentrations of endogenous amino acids. To better understand ligand-transporter interactions that could improve potency, we developed structural LAT1 models to guide the design of substituted analogues of phenylalanine and histidine. Furthermore, we evaluated the structure-activity relationship (SAR) for both enantiomers of naturally occurring LAT1 substrates. Analogues were tested in cis-inhibition and trans-stimulation cell assays to determine potency and uptake rate. Surprisingly, LAT1 can transport amino acid-like substrates with wide-ranging polarities including those containing ionizable substituents. Additionally, the rate of LAT1 transport was generally nonstereoselective even though enantiomers likely exhibit different binding modes. Our findings have broad implications to the development of new treatments for brain disorders and cancer.

Teaching Old Compounds New Tricks: DDQ-Photocatalyzed C?H Amination of Arenes with Carbamates, Urea, and N-Heterocycles

The C?H amination of benzene derivatives was achieved using DDQ as photocatalyst and BocNH2 as the amine source under aerobic conditions and visible light irradiation. Electron-deficient and electron-rich benzenes react as substrates with moderate to good product yields. The amine scope of the reaction comprises Boc-amine, carbamates, pyrazoles, sulfonimides and urea. Preliminary mechanistic investigations indicate arene oxidation by the triplet of DDQ to radical cations with different electrophilicity and a charge transfer complex between the amine and DDQ as intermediate of the reaction.