350595-57-2Relevant articles and documents
Acylative kinetic resolution of racemic methyl-substituted cyclic alkylamines with 2,5-dioxopyrrolidin-1-yl (: R)-2-phenoxypropanoate
Bartashevich, Ekaterina V.,Chulakov, Evgeny N.,Ezhikova, Marina A.,Gruzdev, Dmitry A.,Kodess, Mikhail I.,Korolyova, Marina A.,Krasnov, Victor P.,Levit, Galina L.,Tumashov, Andrey A.,Vakarov, Sergey A.
supporting information, p. 862 - 869 (2022/02/03)
The diastereoselective acylation of a number of racemic methyl-substituted cyclic alkylamines with active esters of 2-phenoxypropanoic acid was studied in detail. The ester of (R)-2-phenoxypropanoic acid and N-hydroxysuccinimide was found to be the most selective agent. The highest stereoselectivity was observed in the kinetic resolution of racemic 2-methylpiperidine in toluene at -40 °C (selectivity factor s = 73) with the predominant formation of (R,R)-amide (93.7% de). To explain the observed stereoselectivity, DFT modelling of the transition states in the reactions of the title acylating agent with 2-methylpiperidine and 2-methylpyrrolidine was performed. The calculated values were in good agreement with experimental data. It has been demonstrated that the acylation proceeds via a concerted mechanism, in which the addition of an amine occurs simultaneously with the elimination of the hydroxysuccinimide fragment. The high stereoselectivity of the (R,R)-amide formation is largely ensured by the lower steric hindrances in the transition states as compared to the formation of (R,S)-amide.
Preparation method of (S)-(4-bromine-2-methylbenzene) (3-N-methylmorpholine) ketone
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Paragraph 0016; 0017; 0018; 0019; 0020; 0021, (2017/07/23)
The invention discloses a preparation method of (S)-(4-bromine-2-methylbenzene) (3-N-methylmorpholine) ketone, and belongs to the technical field of organic synthesis. The invention is characterized in that the preparation method of the (S)-(4-bromine-2-m
NOVEL TRIAZINE COMPOUNDS
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, (2014/02/16)
The present invention relates to novel triazine compounds of formula (1). The present invention also discloses compounds of formula I along with other pharmaceutical ac-ceptable excipients and use of the compounds to modulate the PI3K/ mTOR pathway