33097-38-0Relevant academic research and scientific papers
Deaminative chlorination of aminoheterocycles
Ghiazza, Clément,Faber, Teresa,Gómez-Palomino, Alejandro,Cornella, Josep
, p. 78 - 84 (2021/12/23)
Selective modification of heteroatom-containing aromatic structures is in high demand as it permits rapid evaluation of molecular complexity in advanced intermediates. Inspired by the selectivity of deaminases in nature, herein we present a simple methodology that enables 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 can be converted into C(sp2)?Cl bonds. The method is characterized by its wide functional group tolerance and substrate scope, allowing the modification of >20 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 enables 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. [Figure not available: see fulltext.]
Discovery of Reldesemtiv, a Fast Skeletal Muscle Troponin Activator for the Treatment of Impaired Muscle Function
Ashcraft, Luke,Bergnes, Gustave,Chuang, Chihyuan,Collibee, Scott E.,Durham, Nickie,Garard, Marc,Gardina, Jeffrey,Hartman, James,Hinken, Aaron,Hwee, Darren T.,Jamison, Chris R.,Lu, Kevin,Lu, Pu-Ping,Malik, Fady I.,Marquez, Anna,Morgan, Bradley P.,Morgans, David,Muci, Alexander,Romero, Antonio,Schaletzky, Julia,Valkevich, Ellen,Wang, Wenyue,Warrington, Jeffrey,Xu, Donghong,Yao, Bing
supporting information, p. 14930 - 14941 (2021/11/01)
The discovery of reldesemtiv, a second-generation fast skeletal muscle troponin activator (FSTA) that increases force production at submaximal stimulation frequencies, is reported. Property-based optimization of high throughput screening hit 1 led to compounds with improved free exposure and in vivo muscle activation potency compared to the first-generation FSTA, tirasemtiv. Reldesemtiv demonstrated increased muscle force generation in a phase 1 clinical trial and is currently being evaluated in clinical trials for the treatment of amyotrophic lateral sclerosis.
Selective fluorination by halogen exchange of chlorodiazines and chloropyridines promoted by the 'proton sponge' - Triethylamine tris(hydrogen fluoride) system
Darabantu, Mircea,Lequeux, Thierry,Pommelet, Jean-Claude,Plé, Nelly,Turck, Alain
, p. 739 - 750 (2007/10/03)
The 'proton sponge' - triethylamine tris(hydrogen fluoride) mixtures provide a mild and efficient fluorinating reagent to introduce selectively fluorine atoms by halogen exchange into chlorodiazines and chloronitropyridine series.
The proton sponge-triethylamine tris(hydrogen fluoride) system as a selective nucleophilic fluorinating reagent for chlorodiazines
Darabantu, Mirce,Lequeux, Thierry,Pommelet, Jean-Claude,Plé, Nelly,Turck, Alain,Toupet, Lo?c
, p. 6763 - 6767 (2007/10/03)
The proton sponge-triethylamine tris(hydrogen fluoride) mixture provides a mild and efficient fluorinating - reagent for the selective introduction of a fluorine atom, by halogen exchange, into dichlorodiazines. (C) 2000 Elsevier Science Ltd.
Halogen-Exchange Fluorination of Aromatic Halides with HF or HF-Base
Fukuhara, Tsuyoshi,Yoneda, Norihiko
, p. 509 - 512 (2007/10/02)
Heteroatomic halides such as 2-chloropyrimidines and 2-chloropyridines, and 2,4-dinitrochlorobenzene underwent halogen-exchange fluorination with the treatment of HF or HF-base solutions to afford the corresponding fluorides in good yields.
