15803-02-8Relevant articles and documents
PIPERIDINYL-METHYL-PURINEAMINES AS NSD2 INHIBITORS AND ANTI-CANCER AGENTS
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Page/Page column 54, (2021/02/19)
The present invention provides a compound of Formula (I): (I) or an enantiomer, an enantiomeric mixture, or a pharmaceutically acceptable salt thereof; wherein the variables are as defined herein. The present invention further provides pharmaceutical compositions comprising such compounds; and methods of using such compounds for treating a disease or condition mediated by nuclear SET domain-containing protein 2 (NSD2).
Transition-metal-free decarboxylative bromination of aromatic carboxylic acids
Quibell, Jacob M.,Perry, Gregory J. P.,Cannas, Diego M.,Larrosa, Igor
, p. 3860 - 3865 (2018/04/26)
Methods for the conversion of aliphatic acids to alkyl halides have progressed significantly over the past century, however, the analogous decarboxylative bromination of aromatic acids has remained a longstanding challenge. The development of efficient methods for the synthesis of aryl bromides is of great importance as they are versatile reagents in synthesis and are present in many functional molecules. Herein we report a transition metal-free decarboxylative bromination of aromatic acids. The reaction is applicable to many electron-rich aromatic and heteroaromatic acids which have previously proved poor substrates for Hunsdiecker-type reactions. In addition, our preliminary mechanistic study suggests that radical intermediates are not involved in this reaction, which is in contrast to classical Hunsdiecker-type reactivity. Overall, the process demonstrates a useful method for producing valuable reagents from inexpensive and abundant starting materials.
Photocatalytic Oxidative Bromination of Electron-Rich Arenes and Heteroarenes by Anthraquinone
Petzold, Daniel,K?nig, Burkhard
supporting information, p. 626 - 630 (2017/11/22)
The estimated excited oxidation potential of sodium anthraquinone-2-sulfonate (SAS) increases from 1.8 V to about 2.3 V vs SCE by protonation with Br?nsted acids. This increased photooxidation power of protonated anthraquinone was used for the regio-selective oxidative bromination of electron rich (hetero)arenes and drugs in good yield. The mild reaction conditions are compatible with many functional groups, such as double and triple bonds, ketones, amides and amines, hydroxyl groups, carboxylic acids and carbamates. Mechanistic investigations indicate the photooxidation of the arene followed by nucleophilic bromide addition as the likely pathway. (Figure presented.).
AUTOTAXIN INHIBITOR COMPOUNDS
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Paragraph 00308; 00309, (2015/06/08)
Described herein are compounds that are autotaxin inhibitors, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds in the treatment of conditions, diseases, or disorde
Efficient and Practical Oxidative Bromination and Iodination of Arenes and Heteroarenes with DMSO and Hydrogen Halide: A Mild Protocol for Late-Stage Functionalization
Song, Song,Sun, Xiang,Li, Xinwei,Yuan, Yizhi,Jiao, Ning
supporting information, p. 2886 - 2889 (2015/06/30)
An efficient and practical system for inexpensive bromination and iodination of arenes as well as heteroarenes by using readily available dimethyl sulfoxide (DMSO) and HX (X = Br, I) reagents is reported. This mild oxidative system demonstrates a versatile protocol for the synthesis of aryl halides. HX (X = Br, I) are employed as halogenating reagents when combined with DMSO which participates in the present chemistry as a mild and inexpensive oxidant. This oxidative system is amenable to late-stage bromination of natural products. The kilogram-scale experiment (>95% yield) shows great potential for industrial application.
Crucial role of paramagnetic ligands for magnetostructural anomalies in "breathing crystals"
Tretyakov, Evgeny V.,Tolstikov, Svyatoslav E.,Suvorova, Anastasiya O.,Polushkin, Aleksey V.,Romanenko, Galina V.,Bogomyakov, Artem S.,Veber, Sergey L.,Fedin, Matvey V.,Stass, Dmitry V.,Reijerse, Edward,Lubitz, Wolfgang,Zueva, Ekaterina M.,Ovcharenko, Victor I.
, p. 9385 - 9394 (2012/11/13)
Breathing crystals based on polymer-chain complexes of Cu(hfac)2 with nitroxides exhibit thermally and light-induced magnetostructural anomalies in many aspects similar to a spin crossover. In the present work, we report the synthesis and investigation of a new family of Cu(hfac)2 complexes with tert-butylpyrazolylnitroxides and their nonradical structural analogues. The complexes with paramagnetic ligands clearly exhibit structural rearrangements in the copper(II) coordination units and accompanying magnetic phenomena characteristic for breathing crystals. Contrary to that, their structural analogues with diamagnetic ligands do not undergo rearrangements in the copper(II) coordination environments. This confirms experimentally the crucial role of paramagnetic ligands and exchange interactions between them and copper(II) ions for the origin of magnetostructural anomalies in this family of molecular magnets.
4-AZETIDINYL-1-HETEROARYL-CYCLOHEXANOL ANTAGONISTS OF CCR2
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Page/Page column 40, (2010/06/19)
The present invention comprises compounds of Formula (I). wherein: R1, R2, R3, and R4 are as defined in the specification. The invention also comprises pharmaceutical compositions comprising the compounds of formula (I) and methods of preventing, treating or ameliorating a CCR2 mediated syndrome, disorder or disease, for example, type II diabetes, obesity or asthma, by administering the compounds of formula (I).
[1, 2, 4] TRIAZOLO [1, 5-A] PYRIDINES AS JAK INHIBITORS
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Page/Page column 60; 77, (2010/04/03)
Novel [1,2,4]triazolo[1,5-a]pyridine compounds are disclosed that have a Formula represented by the following: (I). The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, joint disease, inflammation, and others.
Process development and large-scale synthesis of a c-Met kinase inhibitor
Stewart, Gavin W.,Brands, Karel M. J.,Brewer, Sarah E.,Cowden, Cameron J.,Davies, Antony J.,Edwards, John S.,Gibson, Andrew W.,Hamilton, Simon E.,Katz, Jason D.,Keen, Stephen P.,Mullens, Peter R.,Scott, Jeremy P.,Wallace, Debra J.,Wise, Christopher S.
experimental part, p. 849 - 858 (2011/03/20)
A highly convergent synthesis of c-Met kinase inhibitor 1 has been demonstrated on a multikilogram scale using three key fragments: dihalotricyclic core 2, chiral sulfamide side chain 3, and pyrazole boronic ester 4. The chirality in sulfamide side chain 3 was installed using the cheap and readily available starting material (S)-epichlorohydrin. A total of 2.71 kg of 1 were isolated in seven steps (the longest linear sequence).
An improved synthesis of 1-methyl-1H-pyrazole-4-boronic acid pinacol ester and its corresponding lithium hydroxy ate complex: application in Suzuki couplings
Mullens, Peter R.
experimental part, p. 6783 - 6786 (2010/04/27)
An improved synthesis of 1-methyl-1H-pyrazole-4-boronic acid pinacol ester via isolation of the corresponding lithium hydroxy ate complex is described. The hydroxy ate complex is available in one pot from 4-bromo-1-methyl-1H-pyrazole and triisopropyl borate, and is isolated by filtration in high yield. Furthermore, the resulting lithium hydroxy ate complex has long-term bench stability and can be employed directly in Suzuki couplings without the need for added base.
