54879-74-2Relevant academic research and scientific papers
Six-Step Gram-Scale Synthesis of the Human Immunodeficiency Virus Integrase Inhibitor Dolutegravir Sodium
Dietz, Jule-Philipp,Lucas, Tobias,Gro?, Jonathan,Seitel, Sebastian,Brauer, Jan,Ferenc, Dorota,Gupton, B. Frank,Opatz, Till
, p. 1898 - 1910 (2021/08/01)
A short and practical synthesis for preparing the active pharmaceutical ingredient dolutegravir sodium was developed. The convergent strategy starts from (R)-3-amino-1-butanol and establishes the BC ring system in a 76% isolated yield over four steps. Ring A was constructed by a one-pot 1,4-addition to diethyl-(2E/Z)-2-(ethoxymethylidene)-3-oxobutandioate and subsequent MgBr2·OEt2-mediated regioselective cyclization. Amide formation with 2,4-difluorobenzylamine was either performed from the free carboxylic acid or through aminolysis of the corresponding ethyl ester. Final salt formation afforded dolutegravir sodium in a 48-51% isolated yield (HPLC purity of 99.7-99.9%) over six linear steps.
Flexible access to conformationally-locked bicyclic morpholines
Bogacki, Rachael,Gill, Duncan M.,Kerr, William J.,Lamont, Scott,Parkinson, John A.,Paterson, Laura C.
supporting information, p. 8931 - 8933 (2013/09/24)
A preparatively accessible route to a series of conformationally-locked bicyclic morpholines has been developed. This flexible approach allows for diversification in order for a small array of lead-like scaffolds to be synthesised from readily available k
Discovery of 1-arylcarbonyl-6,7-dimethoxyisoquinoline derivatives as glutamine fructose-6-phosphate amidotransferase (GFAT) inhibitors
Qian, Yimin,Ahmad, Mushtaq,Chen, Shaoqing,Gillespie, Paul,Le, Nam,Mennona, Frank,Mischke, Steven,So, Sung-Sau,Wang, Hong,Burghardt Charles,Tannu, Shahid,Conde-Knape, Karin,Kochan, Jarema,Bolin, David
scheme or table, p. 6264 - 6269 (2011/11/29)
Through high throughput screening and subsequent hit identification and optimization, we synthesized a series of 1-arylcarbonyl-6,7- dimethoxyisoquinoline derivatives as the first reported potent and reversible GFAT inhibitors. SAR studies of this class o
A convenient synthesis of indole-substituted 2-pyrrolidones and their cyclized derivatives
Boisbrun, Michel,Jeannin, Laurent,Toupet, Loic,Laronze, Jean-Yves
, p. 3051 - 3057 (2007/10/03)
Condensation between indole, Meldrum's acid, and benzyloxycarbonylacetaldehyde or aminoacetaldehyde derivatives yielded trimolecular adducts 7a-c. The latter were cyclized to indole-substituted 2-pyrrolidones 15a-b or 3-aminopyrrolid-2-ones 18a-b, dependi
