10128-91-3Relevant articles and documents
Highly regiocontrolled and stereocontrolled syntheses of polysubstituted aminocyclohexanes: mild inverse-electron-demand Diels–Alder cycloadditions of electrophilic 2-pyridones
Conyers, Ryan C.,Mazzone, Jennifer R.,Siegler, Maxime A.,Posner, Gary H.
, p. 3344 - 3348 (2016)
Strongly electrophilic N-arenesulfonyl-2-pyridone-3-carboxylate methyl esters complex with zinc dibromide and then react with nucleophilic benzyl vinyl ether or benzyloxyallene to achieve inverse-electron-demand Diels–Alder (IEDDA) cycloadditions. These cycloadducts are produced on gram scale and in 77–89% yields, importantly without the use of high pressure. These 4+2 cycloadditions strongly favor regioselective and stereoselective formation of endo bicyclic lactams as established by X-ray crystallography. These bicyclic lactams undergo useful reactions, including reductive cleavage of the N-sulfonyl group, exo-syn-dihydroxylations, and lactam ring-opening to produce a variety of aminocyclitols.
THROMBIN INHIBITORS, FORMULATIONS, AND USES THEREOF
-
Paragraph 00189, (2020/02/06)
Thrombin-inhibiting acylated pyrazole-pyridone compounds of formula (II) are disclosed herein, as well as pharmaceutical compositions, including tablets, that contain acylated pyrazole- pyridone compounds. These compounds are useful for the treatment and prevention of thrombin-related related diseases and disorders. Processes for making tablets containing acylated pyrazole-pyridones are also included.
Development of a Practical Synthesis of a Peripherally Selective Noradrenaline Reuptake Inhibitor Possessing a Chiral 6,7-trans-Disubstituted-1,4-oxazepane as a Scaffold
Ishimoto, Kazuhisa,Yamaguchi, Kotaro,Nishimoto, Atsushi,Murabayashi, Mika,Ikemoto, Tomomi
, p. 2001 - 2011 (2017/12/26)
A practical synthesis of a peripherally selective noradrenaline reuptake inhibitor that has a chiral 6,7-trans-disubstituted-1,4-oxazepane as a new class of scaffold is described. The amino alcohol possessing the desired stereochemistry was obtained with excellent dr and ee, starting from a commercially available aldehyde via a Morita-Baylis-Hillman reaction, Michael addition, isolation as maleic acid salt, reduction, and diastereomeric salt formation with (+)-10-camphorsulfonic acid. The desired single stereoisomer obtained at an early stage of the synthesis was used for seven-membered ring formation in fully telescoped processes, providing the chiral 6,7-trans-disubstituted-1,4-oxazepane efficiently. In addition to controls of dr and ee of the chiral 1,4-oxazepane, and control of N,O-selectivity in SN2 reaction of the intermediate mesylate with a pyridone derivative, finding appropriate intermediates that were amenable to isolation and upgrade of purity enabled a practical chiral HPLC separation-free, column chromatograph-free synthesis of the drug candidate with excellent chemical and optical purities in a higher overall yield.