53370-50-6Relevant articles and documents
Scalable and Safe Transformation of 3-Hydroxypropionitrile to Its Amidoxime
Hlubb, Leah N.,Johnson, Eric C.,Sabatini, Jesse J.,Orlicki, Joshua A.
, p. 195 - 198 (2022/01/20)
Scalable synthesis of amidoxime 1 by nucleophilic addition of 50% aq. NH2OH to 3-hydroxypropionitrile is reported. In the presence of hydroxyl and amidoxime moieties, this dually functional compound can be manipulated for the synthesis of heterocyclic compounds that may be useful for the energetic materials and pharmaceutical chemistry communities. In preparing 1, it was discovered that previously published procedures were either irreproducible and/or the processes were not practical on larger scales. Previously published procedures required flash chromatography and/or afforded the amidoxime product in a low yield. The improved method discussed in this paper involves rotary evaporation of the completed reaction mixture to remove excess water, followed by trituration in acetone to obtain 83–90% yields. This method has been carried out multiple times on the 86–94 g scale, with minimal exothermic activity detected.
Discovery of N-{5-[3-(3-hydroxypiperidin-1-yl)-1,2,4-oxadiazol-5-yl]-4- methyl-1,3-thiazol-2-yl}acetamide (TASP0415914) as an orally potent phosphoinositide 3-kinase γ inhibitor for the treatment of inflammatory diseases
Oka, Yusuke,Yabuuchi, Tetsuya,Oi, Takahiro,Kuroda, Shoichi,Fujii, Yasuyuki,Ohtake, Hidenori,Inoue, Tomoyuki,Wakahara, Shunichi,Kimura, Kayo,Fujita, Kiyoko,Endo, Mayumi,Taguchi, Kyoko,Sekiguchi, Yoshinori
, p. 7578 - 7583 (2014/01/06)
Class I phosphoinositide 3-kinases (PI3Ks), particularly PI3Kγ, have become attractive drug targets for inflammatory and autoimmune disorders such as rheumatoid arthritis. Herein, we describe the synthesis and the structure-activity relationships (SAR) of a series of 2-amino-5-oxadiazolyl thiazoles, culminating in the identification of 8j (TASP0415914), an orally potent inhibitor of phosphoinositide 3-kinase γ (PI3Kγ). TASP0415914 demonstrated good potency in a cell-based assay and, furthermore, exhibited in vivo efficacy in a collagen induced arthritis (CIA) model in mice after oral administration.
NOVEL NITRILE AND AMIDOXIME COMPOUNDS AND METHODS OF PREPARATION
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, (2009/05/28)
The present application relates to semiconductor processing compositions comprising at least one compound containing at least one amidoxime functional group and to methods of using these compositions in semiconductor processing. The present application also describes the preparation of amidoximes for a semiconductor processing composition by (a) mixing a cyanoethylation catalyst, a nucleophile and an alpha-unsaturated nitrile to produce a cyanoethylation product; and (b) converting a cyano group in the cyanoethylation product into an amidoxime functional group.