37590-23-1Relevant academic research and scientific papers
One-Step Synthesis of 3,4-Disubstituted 2-Oxazolidinones by Base-Catalyzed CO2 Fixation and Aza-Michael Addition
Mannisto, Jere K.,Sahari, Aleksi,Lagerblom, Kalle,Niemi, Teemu,Nieger, Martin,Sztanó, Gábor,Repo, Timo
supporting information, p. 10284 - 10289 (2019/08/01)
2-Oxazolidinones are saturated heterocyclic compounds, which are highly attractive targets in modern drug design. Herein, we describe a new, single-step approach to 3,4-disubstituted 2-oxazolidinones by aza-Michael addition using CO2 as a carbonyl source and 1,1,3,3-tetramethylguanidine (TMG) as a catalyst. The modular reaction, which occurs between a γ-brominated Michael acceptor, CO2 and an arylamine, aliphatic amine or phenylhydrazine, is performed under mild conditions. The regiospecific reaction displays good yields (av. 75 %) and excellent functional-group compatibility. In addition, late-stage functionalization of drug and drug-like molecules is demonstrated. The experimental results suggest a mechanism consisting of several elementary steps: TMG-assisted carboxylation of aniline; generation of an O-alkyl carbamate; and the final ring-forming step through an intramolecular aza-Michael addition.
KRAS G12C INHIBITORS
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Paragraph 0969-0970, (2019/05/24)
The present invention relates to compounds that inhibit KRas G12C. In particular, the present invention relates to compounds that irreversibly inhibit the activity of KRas G12C, pharmaceutical compositions comprising the compounds and methods of use therefor.
KRAS G12C INHIBITORS
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Paragraph 0584, (2017/12/18)
The present invention relates to compounds that inhibit KRas G12C. In particular, the present invention relates to compounds that irreversibly inhibit the activity of KRas G12C, pharmaceutical compositions comprising the compounds and methods of use therefor.
Cephalosporin derivatives and processes for the preparation thereof
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, (2008/06/13)
PCT No. PCT/KR96/00255 Sec. 371 Date Jun. 26, 1998 Sec. 102(e) Date Jun. 26, 1998 PCT Filed Dec. 27, 1996 PCT Pub. No. WO97/24359 PCT Pub. Date Jul. 10, 1997The invention provides novel cephalosporin derivatives of the formula (I) and salts thereof for use in pharmaceutical compositions. Also novel precursors for synthesis of the cephalosporins are disclosed.
Synthesis of Novel Dihydrothiazolopyrimidinone Derivatives
Selby, T. P.,Smith, B. K.
, p. 1237 - 1240 (2007/10/02)
Condensation of 2-amino-4-hydroxy-2-mercaptopyrimidine (2) hydrate and ethyl 4-bromocrotonate gave a mixture of ethyl 7-amino-2,3-dihydro-5-oxo-5H-thiazolopyrimidine-3-acetate (4) and 2a,3-dihydro-1-thia-5,8,8b-triazaacenaphthylene-4,7(2H)-dione (5) whereas reaction of 2 with 4-bromocrotononitrile afforded only 7-amino-2,3-dihydro-5-oxo-5H-thiazolopyrimidine-3-acetonitrile.Reaction of the tricycle 5 (which was isolated as a hemihydrate) with excess methyl iodide/potassium carbonate in dimethylformamide resulted in both ring hydrolysis and methylaion to give 3,4-dihydro-1,7-dimethyl-4--2H-pyrimidopyrimidine-2,6,8(1H,7H)-trione (10).Methylating 5 with excess methyl iodide/sodium methoxide in methanol also resulted in ring fragmentation and methylation but instead afforded methyl 7-methylamino-2,3-dihydro-5-oxo-7H-thiazolopyrimidine-3-acetate.The mechanistic aspects of these reactions are discussed.
