Tag: M.W:300-400

El Khatib, Mirna; Serafim, Ricardo Augusto Massarico; Molander, Gary A. published the artcile< α-Arylation/Heteroarylation of Chiral α-Aminomethyltrifluoro-borates by Synergistic Iridium Photoredox/Nickel Cross-Coupling Catalysis>, SDS of cas: 374930-88-8, the main research area is arylation heteroarylation aminomethyltrifluoroborate iridium photoredox nickel cross coupling catalyst; amino acids; cross-coupling; heterocycles; nickel; photochemistry.

Direct access to complex, enantiopure benzylamine architectures using a synergistic iridium photoredox/nickel cross-coupling dual catalysis strategy has been developed. New C(sp3)-C(sp2) bonds are forged starting from abundant and inexpensive natural amino acids.

Angewandte Chemie, International Edition published new progress about Amino acid esters Role: RCT (Reactant), RACT (Reactant or Reagent). 374930-88-8 belongs to class piperazines, and the molecular formula is C13H19BrN4O2, SDS of cas: 374930-88-8.

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Yang, Yang; Niedermann, Katrin; Han, Chong; Buchwald, Stephen L. published the artcile< Highly Selective Palladium-Catalyzed Cross-Coupling of Secondary Alkylzinc Reagents with Heteroaryl Halides>, Category: piperazines, the main research area is secondary alkylzinc Negishi coupling heteroaryl halide palladium biarylphosphine catalyst.

The highly selective palladium-catalyzed Negishi coupling of secondary alkylzinc reagents with heteroaryl halides is described [e.g., using a palladacycle precatalyst ligated by CPhos, 3-chlorobenzisothiazole was coupled with i-PrZnBr.LiCl to afford 3-isopropylbenzisothiazole in 78% yield (normal:rearranged ratio = 98:2)]. The development of a series of biarylphosphine ligands has led to the identification of an improved catalyst for the coupling of electron-deficient heterocyclic substrates. Preparation and characterization of oxidative addition complex (L)(Ar)PdBr provided insight into the unique reactivity of catalysts based on CPhos-type ligands in facilitating challenging reductive elimination processes.

Organic Letters published new progress about Aromatic nitrogen heterocycles Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (heteroaryl halides → sec-alkyl heteroaryl compounds). 374930-88-8 belongs to class piperazines, and the molecular formula is C13H19BrN4O2, Category: piperazines.

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Yamamoto, Eiji; Ukigai, Satoshi; Ito, Hajime published the artcile< Boryl substitution of functionalized aryl-, heteroaryl- and alkenyl halides with silylborane and an alkoxy base: expanded scope and mechanistic studies>, Formula: C13H19BrN4O2, the main research area is arylbromide dimethylphenylsilyl boronic acid pinacol ester borylation; boronic acid pinacol ester aryl preparation; aryl iodide aryl boronate Suzuki coupling biaryl preparation; alkenyl halide dimethylphenylsilyl boronic acid pinacol ester borylation; alkenylboronate preparation.

A transition-metal-free method was developed for the boryl substitution of functionalized aryl-, heteroaryl- and alkenyl halides with a silylborane in the presence of an alkali-metal alkoxide. The base-mediated boryl substitution of organohalides with a silylborane was recently reported to provide the corresponding borylated products in good to high yields, and exhibit good functional group compatibility and high tolerance to steric hindrance. The scope of this transformation was extended significantly to include a wide variety of functionalized aryl-, heteroaryl- and alkenyl halides. In particular, the boryl substitution of (E)- and (Z)-alkenyl halides proceeded smoothly to afford the corresponding alkenyl boronates in good to high yields with retention of the configuration using modified reaction conditions. The results of the mechanistic studies suggest that this boryl substitution proceeds via a carbanion-mediated mechanism.

Chemical Science published new progress about Aryl halides Role: RCT (Reactant), RACT (Reactant or Reagent). 374930-88-8 belongs to class piperazines, and the molecular formula is C13H19BrN4O2, Formula: C13H19BrN4O2.

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Rabal, Obdulia; Sanchez-Arias, Juan A.; Cuadrado-Tejedor, Mar; de Miguel, Irene; Perez-Gonzalez, Marta; Garcia-Barroso, Carolina; Ugarte, Ana; Estella-Hermoso de Mendoza, Ander; Saez, Elena; Espelosin, Maria; Ursua, Susana; Haizhong, Tan; Wei, Wu; Musheng, Xu; Garcia-Osta, Ana; Oyarzabal, Julen published the artcile< Design, Synthesis, and Biological Evaluation of First-in-Class Dual Acting Histone Deacetylases (HDACs) and Phosphodiesterase 5 (PDE5) Inhibitors for the Treatment of Alzheimer's Disease>, Electric Literature of 374930-88-8, the main research area is histone deacetylase HDAC phosphodiesterase PDE5 inhibitor antialzheimer Alzheimer.

Simultaneous inhibition of phosphodiesterase 5 (PDE5) and histone deacetylases (HDAC) has recently been validated as a potentially novel therapeutic approach for Alzheimer’s Disease (AD). To further extend this concept, the authors designed and synthesized the first chem. series of dual acting PDE5 and HDAC inhibitors, and the authors validated this systems therapeutics approach. Following the implementation of structure- and knowledge-based approaches, initial hits were designed and were shown to validate the hypothesis of dual in vitro inhibition. Then, an optimization strategy was pursued to obtain a proper tool compound for in vivo testing in AD models. Initial hits were translated into mols. with adequate cellular functional responses (histone acetylation and cAMP/cGMP response element-binding (CREB) phosphorylation in the nanomolar range), an acceptable therapeutic window (>1 log unit) and the ability to cross the blood-brain barrier, leading to the identification of 7 as a candidate for in vivo proof-of-concept testing.

Journal of Medicinal Chemistry published new progress about Alzheimer disease. 374930-88-8 belongs to class piperazines, and the molecular formula is C13H19BrN4O2, Electric Literature of 374930-88-8.

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Tellis, John C.; Amani, Javad; Molander, Gary A. published the artcile< Single-Electron Transmetalation: Photoredox/Nickel Dual Catalytic Cross-Coupling of Secondary Alkyl β-Trifluoroboratoketones and -esters with Aryl Bromides>, Recommanded Product: tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate, the main research area is secondary alkyltrifluoroborate aryl bromide cross coupling photoredox nickel catalyst; aralkyl ketone preparation; ester aralkyl preparation.

The first cross-coupling of secondary alkyl β-trifluoroboratoketones and -esters has been achieved through application of photoredox/nickel dual catalysis. Although the related β-trifluoroboratoamides have been effectively cross-coupled via Pd-catalysis, the corresponding ketones and esters had proven recalcitrant prior to this report. Reactions occur under mild conditions, and a variety of functional groups and sterically and electronically diverse reaction partners are tolerated.

Organic Letters published new progress about Aralkyl ketones Role: SPN (Synthetic Preparation), PREP (Preparation). 374930-88-8 belongs to class piperazines, and the molecular formula is C13H19BrN4O2, Recommanded Product: tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate.

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Phelan, James P.; Wiles, Rebecca J.; Lang, Simon B.; Kelly, Christopher B.; Molander, Gary A. published the artcile< Rapid access to diverse, trifluoromethyl-substituted alkenes using complementary strategies>, Application In Synthesis of 374930-88-8, the main research area is trifluoromethyl alkene preparation; silyl alc trifluoromethyl cross coupling palladium; Peterson elimination; organotrifluoroborate cross coupling palladium.

Two synergistic approaches to the facile assembly of complex α-trifluoromethyl alkenes are described. Using α-trifluoromethyl-β-silyl alcs. as masked trifluoromethyl alkenes, cross-coupling or related functionalization processes at distal electrophilic sites can be executed without inducing Peterson elimination. Subsequent Lewis acidic activation affords functionalized α-trifluoromethyl alkenes. Likewise, the development of a novel α-trifluoromethylvinyl trifluoroborate reagent complements this approach and allows a one-step cross-coupling of (hetero)aryl halides to access a broad array of complex α-trifluoromethyl alkenes.

Chemical Science published new progress about Addition reaction. 374930-88-8 belongs to class piperazines, and the molecular formula is C13H19BrN4O2, Application In Synthesis of 374930-88-8.

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

De Savi, Chris; Waterson, David; Pape, Andrew; Lamont, Scott; Hadley, Elma; Mills, Mark; Page, Ken M.; Bowyer, Jonathan; Maciewicz, Rose A. published the artcile< Hydantoin based inhibitors of MMP13-Discovery of AZD6605>, Application of C13H19BrN4O2, the main research area is piperidine ether aryl piperazine hydantoin inhibitor MMP13 osteoarthritis; Cyp P450; Hydantoin; Lead optimisation; MMP13; Zinc binder.

Piperidine ether and aryl piperazine hydantoins are reported as potent inhibitors of MMP13. A medicinal chem. campaign focused on replacing the reverse hydroxamate zinc binding group associated with historical inhibitors with a hydantoin zinc binding group then optimizing MMP13 potency, solubility and DMPK properties while maintaining good selectivity over MMP14. A number of high quality candidates were progressed and following rat and dog safety evaluation, AZD6605 (3m) was identified as a candidate drug.

Bioorganic & Medicinal Chemistry Letters published new progress about Enzyme inhibitors. 374930-88-8 belongs to class piperazines, and the molecular formula is C13H19BrN4O2, Application of C13H19BrN4O2.

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Jouffroy, Matthieu; Kelly, Christopher B.; Molander, Gary A. published the artcile< Thioetherification via Photoredox/Nickel Dual Catalysis>, Application In Synthesis of 374930-88-8, the main research area is thioether aryl heteroaryl preparation; aryl heteroaryl bromide thioetherification thiol hypervalent alkylsilicate nickel photoredox.

Hypervalent alkylsilicates represent new and readily accessible precursors for the generation of alkyl radicals under photoredox conditions. Alkyl radicals generated from such silicates serve as effective hydrogen atom abstractors from thiols, furnishing thiyl radicals. The reactive sulfur species generated in this manner can be funneled into a nickel-mediated cross-coupling cycle employing aromatic bromides to furnish thioethers. The serendipitous discovery of this reaction and its utilization for the thioetherification of various aryl and heteroaryl bromides with a diverse array of thiols are described. The S-H selective H atom abstraction event enables a wide range of functional groups, including those bearing protic moieties, to be tolerated.

Organic Letters published new progress about Aryl bromides Role: RCT (Reactant), RACT (Reactant or Reagent). 374930-88-8 belongs to class piperazines, and the molecular formula is C13H19BrN4O2, Application In Synthesis of 374930-88-8.

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Jung, Woo-Ok; Mai, Binh Khanh; Spinello, Brian J.; Dubey, Zachary J.; Kim, Seung Wook; Stivala, Craig E.; Zbieg, Jason R.; Liu, Peng; Krische, Michael J. published the artcile< Enantioselective Iridium-Catalyzed Allylation of Nitroalkanes: Entry to β-Stereogenic α-Quaternary Primary Amines>, Reference of 374930-88-8, the main research area is homoallylic nitroalkane preparation enantioselective; nitroalkane allylic acetate allylation iridium catalyst.

The first systematic study of simple nitronate nucleophiles in iridium-catalyzed allylic alkylation was described. Using a tol-BINAP-modified π-allyliridium C,O-benzoate catalyst, α,α-disubstituted nitronates substitute racemic branched alkyl-substituted allylic acetates, thus providing homoallylic nitroalkanes. DFT calculations revealed early transition states that render the reaction less sensitive to steric effects and distinct trans-effects of diastereomeric chiral-at-iridium π-allyl complexes that facilitate formation of congested tertiary-quaternary C-C bonds.

Journal of the American Chemical Society published new progress about Alkanes, nitro Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 374930-88-8 belongs to class piperazines, and the molecular formula is C13H19BrN4O2, Reference of 374930-88-8.

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Yang, Yang; Buchwald, Stephen L. published the artcile< Ligand-Controlled Palladium-Catalyzed Regiodivergent Suzuki-Miyaura Cross-Coupling of Allylboronates and Aryl Halides>, Computed Properties of 374930-88-8, the main research area is ligand controlled palladium catalyzed regiodivergent Suzuki allylboronate aryl halide.

An orthogonal set of catalyst systems has been developed for the Suzuki-Miyaura coupling of 3,3-disubstituted and 3-monosubstituted allylboronates with (hetero)aryl halides. These methods allow for the highly selective preparation of either the α- or the γ-isomeric coupling product [e.g., 1-butyl-4-prenylbenzene or 1-butyl-4-(2-methylbut-3-en-2-yl)benzene from reaction of 1-bromo-4-butylbenzene with prenylboronic acid pinacol ester].

Journal of the American Chemical Society published new progress about Aryl halides Role: RCT (Reactant), RACT (Reactant or Reagent) (and heteroaryl). 374930-88-8 belongs to class piperazines, and the molecular formula is C13H19BrN4O2, Computed Properties of 374930-88-8.

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics