151-00-8Relevant articles and documents
Hine et al.
, p. 5186,5190, 5193 (1970)
Process development and multikilogram syntheses of XL228 utilizing a regioselective isoxazole formation and a selective SNAr reaction to a pyrimidine core
Guz, Nathan R.,Leuser, Helena,Goldman, Erick
, p. 1066 - 1073 (2013)
Route scouting, process development, and multikilogram syntheses of an IGF-1R/Src/Bcr-Abl inihibitor are reported. Key aspects of the developed route are a regioselective [3 + 2] isoxazole formation on a pyrimidine core and a selective SNAr addition of an aryl amine to a symmetrical dichloro substituted pyrimidine. The route contains six synthetic steps and was demonstrated twice on scale, delivering 4.6 and 11.2 kg (25% and 16% overall yield), for Phase I clinical studies.
COMPOUNS, COMPOSITIONS AND METHODS OF USE
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Page/Page column 171, (2018/07/29)
Herein, compounds, compositions and methods for modulating inclusion formation and stress granules in cells related to the onset of neurodegenerative diseases, musculoskeletal diseases, cancer, ophthalmological diseases, and viral infections are described.
An Efficient One–pot Procedure for the Direct Preparation of 4,5-Dihydroisoxazoles from Amides
Slagbrand, Tove,Kervefors, Gabriella,Tinnis, Fredrik,Adolfsson, Hans
supporting information, p. 1990 - 1995 (2017/06/09)
A Mo(CO)6 (molybdenumhexacarbonyl) catalyzed reductive functionalization of amides to afford 5-amino substituted 4,5-dihydroisoxazoles is presented. The reduction of amides generates reactive enamines, which upon the addition of hydroximinoyl chlorides and base undergoes a 1,3-dipolar cycloaddition reaction that gives access to the desired heterocyclic compounds. The transformation of amides is highly chemoselective and tolerates functional groups such as nitro, nitriles, esters, and ketones. Furthermore, a versatile scope of 4,5-dihydroisoxazoles derived from a variety of hydroximinoyl chlorides and amides is demonstrated. (Figure presented.).
