Month: December 2022

Wang, Peng published the artcileLigand-Promoted Meta-C-H Arylation of Anilines, Phenols, and Heterocycles, Quality Control of 90778-25-9, the publication is Journal of the American Chemical Society (2016), 138(29), 9269-9276, database is CAplus and MEDLINE.

The authors report the development of a versatile 3-acetylamino-2-hydroxypyridine class of ligands that promote meta-C-H arylation of anilines, heterocyclic aromatic amines, phenols, and 2-benzyl heterocycles using norbornene as a transient mediator. More than 120 examples are presented, demonstrating this ligand scaffold enables a wide substrate and coupling partner scope. Meta-C-H arylation with heterocyclic aryl iodides as coupling partners is also realized for the first time using this ligand. The utility for this transformation for drug discovery is showcased by allowing the meta-C-H arylation of a lenalidomide derivative The first steps toward a silver-free protocol for this reaction are also demonstrated.

Journal of the American Chemical Society published new progress about 90778-25-9. 90778-25-9 belongs to pyridine-derivatives, auxiliary class Trifluoromethyl,Pyridine,Fluoride,Amine,Alcohol, name is 3-Amino-5-(trifluoromethyl)pyridin-2-ol, and the molecular formula is C17H14N2O2, Quality Control of 90778-25-9.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Zhao, Jing published the artcileA liquid chromatography-mass spectrometry workflow for in-depth quantitation of fatty acid double bond location isomers, COA of Formula: C12H9NO, the publication is Journal of Lipid Research (2021), 100110, database is CAplus and MEDLINE.

Tracing compositional changes of fatty acids (FAs) is frequently used as a means of monitoring metabolic alterations in perturbed biol. states. Given that more than half of FAs in the mammalian lipidome are unsaturated, quantitation of FAs at a carbon-carbon double bond (C=C) location level is necessary. The use of 2-acetylpiridine (2-acpy) as the charge-tagging PB reagent led to a limit of identification in the subnanomolar range for mono- and polyunsaturated as well as conjugated FAs. Conjugated free FAs of low abundance such as FA 18:2 (n-7, n-9) and FA 18:2 (n-6, n-8) were quantified at concentrations of 0.61 ± 0.05 and 0.05 ± 0.01 mg per 100 g in yak milk powder, resp. This workflow also enabled deep profiling of eight saturated and 37 unsaturated total FAs across a span of four orders of magnitude in concentration, including ten groups of C=C location isomers in pooled human plasma. A pilot survey on total FAs in plasma from patients with type 2 diabetes revealed that the relative compositions of FA 16:1 (n-10) and FA 18:1 (n-10) were significantly elevated compared with that of normal controls. In this work, we have developed a workflow for global quantitation of FAs, including C=C location isomers, via charge-tagging Paterno-Buchi (PB) derivatization and liquid chromatog.-tandem mass spectrometry (LC-MS/MS).

Journal of Lipid Research published new progress about 91-02-1. 91-02-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Benzene,Ketone, name is Phenyl(pyridin-2-yl)methanone, and the molecular formula is C21H24O8, COA of Formula: C12H9NO.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Dai, Jian-Jun published the artcileCopper-Promoted Sandmeyer Trifluoromethylation Reaction, HPLC of Formula: 39856-58-1, the publication is Journal of the American Chemical Society (2013), 135(23), 8436-8439, database is CAplus and MEDLINE.

A copper-promoted trifluoromethylation reaction of aromatic amines is described. This transformation proceeds smoothly under mild conditions and exhibits good tolerance of many synthetically relevant functional groups. It provides an alternative approach for the synthesis of trifluoromethylated arenes and heteroarenes. It also constitutes a new example of the Sandmeyer reaction.

Journal of the American Chemical Society published new progress about 39856-58-1. 39856-58-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Bromide,Amine, name is 2-Bromopyridin-3-amine, and the molecular formula is C5H5BrN2, HPLC of Formula: 39856-58-1.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Liu, Yanjie published the artcileFeCl₂ Catalyzed Three-Component Reactions of Phospholes, Pyrrolidine, and Ketones (Aldehydes): Chemoselective Synthesis of 1-Phosphafulvenes, Quality Control of 91-02-1, the publication is Organic Letters (2021), 23(8), 2943-2947, database is CAplus and MEDLINE.

The authors have developed an unprecedented approach for the synthesis of transient 1-phosphafulvenes through three component reactions of phospholes. The generation of 1-phosphafulvenes was demonstrated by in situ [6 + 4] cycloaddition with 2H-phospholes and [6 + 6] self-dimerization. The [6 + 4] and [6 + 6] reaction pathway could be modulated by the starting ketones and aldehydes. The construction of 1-phosphafulvenes is illustrated by a proposed mechanism combining nucleophilic addition of phospholide to the iminium or isomerized azomethine ylide and a [1,5]-shift of phosphole.

Organic Letters published new progress about 91-02-1. 91-02-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Benzene,Ketone, name is Phenyl(pyridin-2-yl)methanone, and the molecular formula is C12H9NO, Quality Control of 91-02-1.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Xing, Kai published the artcileA self-calibrating dual responsive platform for the sensitive detection of sulfite and sulfonic derivatives based on a robust Hf(IV) metal-organic framework, Computed Properties of 636-73-7, the publication is Chemical Communications (Cambridge, United Kingdom) (2020), 56(4), 631-634, database is CAplus and MEDLINE.

A robust hafnium-based metal organic framework, Hf-PBTA, with sensitive and self-calibrating dual-emissive fluorescence response towards sulfite and sulfonic derivatives, including antibiotic sulfamethazine, has been developed, which shows fast detection of sulfite ions at a concentration as low as 76 ppb. The opposite response tendency from two radiative pathways towards aromatic sulfonic mols. and sulfite anions stems from the synergistic effect of the pyridine protonation effect, π-π stacking interaction and intramol. twist motion.

Chemical Communications (Cambridge, United Kingdom) published new progress about 636-73-7. 636-73-7 belongs to pyridine-derivatives, auxiliary class Pyridine,Sulfonic acid, name is Pyridine-3-sulfonic acid, and the molecular formula is C15H14O3, Computed Properties of 636-73-7.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Alo, Babajide I. published the artcileDirected metalation of pyridinesulfonamides. Synthesis of pyridine-fused isothiazoles and 1,2-oxathioles, Application of Pyridine-3-sulfonic acid, the publication is Journal of Heterocyclic Chemistry (1992), 29(1), 61-4, database is CAplus.

4-Lithio-N–tert-butylpyridine-3-sulfonamide reacted with Ph₂CO or CO₂ to give the corresponding intermediates, which on appropriate treatment gave the addition product I (from Ph₂CO reaction product) or isothiazolo[5,4-c]pyridin-3-one 1,1-dioxides II (R = H, Me₃C) (from CO₂ reaction product). Metalation of 2- and 4-[N,N-(dialkylamino)sulfonyl]pyridines with LiN(CHMe₂)₂ gave anions which reacted with Ph₂CO to give carbinols, which cyclized thermally to 1,2-oxathiolo[3,4-b]- III and -[4,3-c]pyridine dioxide IV, resp.

Journal of Heterocyclic Chemistry published new progress about 636-73-7. 636-73-7 belongs to pyridine-derivatives, auxiliary class Pyridine,Sulfonic acid, name is Pyridine-3-sulfonic acid, and the molecular formula is C5H5NO3S, Application of Pyridine-3-sulfonic acid.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Bew, Sean P. published the artcileOrganocatalytic Aziridine Synthesis Using F⁺ Salts, Product Details of C6H5F4NO3S, the publication is Organic Letters (2009), 11(20), 4552-4555, database is CAplus and MEDLINE.

This paper describes a unique application of the fluoronium cation (F⁺) as an organocatalyst for mediating the reaction between N-substituted imines and Et diazoacetate affording excellent yields of N-substituted aziridines. E.g., N-fluoropyridinium triflate catalyzed the reaction of (E)-N-arylimine I with Et diazoacetate to give 83% cis-aziridine II.

Organic Letters published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C6H5F4NO3S, Product Details of C6H5F4NO3S.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Reich, Marvin F. published the artcilePyrido[3,4-e]-1,2,4-triazines and related heterocycles as potential antifungal agents, Recommanded Product: 4-Amino-2-picoline, the publication is Journal of Medicinal Chemistry (1989), 32(11), 2474-85, database is CAplus and MEDLINE.

The preparation and biol. activities of a series of pyrido[3,4-e]-1,2,4-triazines I (R = H, alkyl, CF₃, cycloalkyl, Ph, substituted Ph, 2-naphthyl, pyridyl, CH:CHNR¹₂, where NR¹₂ = dimethylamino, piperidino, or 4-methylpiperazino), 1,2,4-triazino[5,6-c]quinolines II (R = H, Me, 4-pyridyl), and related fused triazines are described. Methyl, amino, and acylamino substituents were placed in the pyridyl ring of the former system. In agar dilution assays, active compounds in this series, e.g., I (R = H, Me, CH₂OPh, Ph, 4-FC₆H₄, 3-FC₆H₄, 3,4-F₂C₆H₃, 3-, 4-pyridyl) inhibited strains of Candida, Aspergillus, Mucor, and Trichophyton species at MIC’s of ≤16μg/mL.

Journal of Medicinal Chemistry published new progress about 18437-58-6. 18437-58-6 belongs to pyridine-derivatives, auxiliary class Pyridine,Amine, name is 4-Amino-2-picoline, and the molecular formula is C6H8N2, Recommanded Product: 4-Amino-2-picoline.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Ghiazza, Clement published the artcileDeaminative chlorination of aminoheterocycles, SDS of cas: 18437-58-6, the publication is Nature Chemistry (2022), 14(1), 78-84, database is CAplus and MEDLINE.

Herein we present a simple methodol. that enabled the NH₂ groups in aminoheterocycles to be conceived as masked modification handles. With the aid of a simple pyrylium reagent and a cheap chloride source, C(sp²)-NH₂ could be converted into C(sp²)-Cl bonds. The method was characterized by its wide functional group tolerance and substrate scope, allowing the modification of different classes of heteroaromatic motifs (five- and six-membered heterocycles), bearing numerous sensitive motifs. The facile conversion of NH₂ into Cl in a late-stage fashion enabled practitioners to apply Sandmeyer- and Vilsmeier-type transforms without the burden of explosive and unsafe diazonium salts, stoichiometric transition metals or highly oxidizing and unselective chlorinating agents.

Nature Chemistry published new progress about 18437-58-6. 18437-58-6 belongs to pyridine-derivatives, auxiliary class Pyridine,Amine, name is 4-Amino-2-picoline, and the molecular formula is C6H8N2, SDS of cas: 18437-58-6.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Elleraas, Jeff published the artcileConformational Studies and Atropisomerism Kinetics of the ALK Clinical Candidate Lorlatinib (PF-06463922) and Desmethyl Congeners, Recommanded Product: (R)-Methyl 2-(1-((2-amino-5-bromopyridin-3-yl)oxy)ethyl)-4-fluorobenzoate, the publication is Angewandte Chemie, International Edition (2016), 55(11), 3590-3595, database is CAplus and MEDLINE.

Lorlatinib (PF-06463922) is an ALK/ROS1 inhibitor and is in clin. trials for the treatment of ALK pos. or ROS1 pos. NSCLC (i.e. specific subsets of NSCLC). One of the laboratory objectives for this mol. indicated that it would be desirable to advance a mol. which was CNS penetrant in order to treat brain metastases. From this perspective, a macrocyclic template was attractive for a number of reasons. In particular, this template reduces the number of rotatable bonds, provides the potential to shield polar surface area and reinforces binding through a restricted conformation. All of these features led to better permeability for the mols. of interest and thus increased the chance for better blood brain barrier penetration. With a CNS penetrant mol., kinase selectivity is a key consideration particularly with regard to proteins such as TrkB, which are believed to influence cognitive function. Removal of the chiral benzylic Me substituent from lorlatinib was perceived as not only a means to simplify synthetic complexity, but also as a strategy to further truncate the mol. of interest. Examination of the NMR of the desmethyl analogs revealed that the compound existed as a mixture of atropisomers, which proved separable by chiral SFC. The individual atropisomers were evaluated through a series of in vitro assays, and shown to have a favorable selectivity profile when compared to lorlatinib. The challenge to develop such a mol. lies in the rate at which the atropisomers interchange dictated by the energy barrier required to do this. Here, we describe the synthesis of the desmethyl macrocycles, conformational studies on the atropisomers, and the kinetics of the interconversion. In addition, the corresponding conformational studies on lorlatinib are reported providing a hypothesis for why a single diastereomer is observed when the chiral benzylic Me group is introduced.

Angewandte Chemie, International Edition published new progress about 1454848-00-0. 1454848-00-0 belongs to pyridine-derivatives, auxiliary class Aromatic Fluorinated Building Blocks, name is (R)-Methyl 2-(1-((2-amino-5-bromopyridin-3-yl)oxy)ethyl)-4-fluorobenzoate, and the molecular formula is C15H14BrFN2O3, Recommanded Product: (R)-Methyl 2-(1-((2-amino-5-bromopyridin-3-yl)oxy)ethyl)-4-fluorobenzoate.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem