- A solution-phase strategy for the synthesis of chemical libraries containing small organic molecules: A universal and dipeptide mimetic template
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A general approach to the solution phase, parallel synthesis of chemical libraries, which allows the preparation of multi-milligram quantities of each individual member, is exemplified with both a universal and dipeptide mimetic template. In each step of the sequence, the reactants, unreacted starting material, reagents and their byproducts are removed by simple liquid/liquid or liquid/solid extractions providing the desired intermediates and final compounds in high purities (290-100%) independent of the reaction yields and without deliberate reaction optimization.
- Cheng, Soan,Tarby, Christine M.,Comer, Daniel D.,Williams, John P.,Caporale, Lynn H.,Myers, Peter L.,Boger, Dale L.
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Read Online
- Multigram Synthesis of Heterabicyclo[n.1.0]alkan-1-yl Trifluoroborates
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An approach to the synthesis of oxa- and azabicyclo[n.1.0]alkan-1-yl trifluoroborates on a multigram scale was developed. Two synthetic strategies were evaluated: the first based on the lithiation–borylation of the corresponding 2-bromoallyl derivatives, and the other relying on regioselective hydroboration of the appropriate hetera-substituted enynes. The second method appeared to be more efficient in terms of scalability and substrate scope. Further steps included ring closing-metathesis, mild palladium-catalyzed cyclopropanation with diazomethane, and reaction with KHF2 and furnished the title compounds in up to 50 g scale in a single run (10–41 % overall yield, 4–5 steps).
- Kleban, Ihor,Krokhmaliuk, Yevhen,Reut, Sofiia,Shuvakin, Serhii,Pendyukh, Vyacheslav V.,Khyzhan, Oleksandr I.,Yarmoliuk, Dmytro S.,Tymtsunik, Andriy V.,Rassukana, Yuliya V.,Grygorenko, Oleksandr O.
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Read Online
- Palladium-catalyzed intermolecular [4 + 2] formal cycloaddition with (Z)-3-iodo allylic nucleophiles and allenamides
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A highly chemo- and regioselective [4 + 2] formal cycloaddition of (Z)-3-iodo allylic nucleophiles and allenamides catalyzed by palladium is reported. The methodology proceeds under mild reaction conditions and is tolerant of alkyl and aryl functional groups. The SN2′ substitution at the proximal C═C bond performed against the Heck or SN2 pathway delivered a variety of 2-amino-dihydropyrans and 2-amino-tetrahydropiperidines in moderate to satisfactory yields. The [4 + 2] formal cycloaddition derivatives are convertible to interesting scaffolds 2,6,7,7a-tetrahydropyrano[2,3-b]pyrrole and 2,6,7,7a-tetrahydro-1H-pyrrolo[2,3-b]pyridine derivatives via ring-closing metathesis (RCM) with Grubbs catalyst II.
- Yan, Fachao,Liang, Hanbing,Ai, Bing,Liang, Wenjing,Jiao, Luyang,Yao, Shuzhi,Zhao, Pingping,Liu, Qing,Dong, Yunhui,Liu, Hui
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p. 2651 - 2656
(2019/03/12)
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- Ternary fused ring substituted six-membered ring derivatives and their use in medicine
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The invention relates to a fused tricyclic substituted amino six-membered ring derivative and application thereof in medicine, particularly a fused tricyclic substituted amino six-membered ring derivative shown in a formula (I) or stereoisomers and pharmaceutically acceptable salts or pro-drugs of the derivative, a pharmaceutical composition comprising the derivative and use of the derivative in preparing a dipeptidyl peptidase IV (DPP-IV) inhibitor in medicine, wherein the substituents in the formula (I) are defined as in the description. The formula (I) is shown in the description.
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Paragraph 0191-0193
(2019/01/22)
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- West request acid bei geleg sandbank and intermediate preparation method
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The invention relates to a preparation method of besigliptin and its intermediate, and concretely relates to a preparation method of an azadicyclic compound besigliptin and its key intermediate. The preparation method comprises the following steps: carrying out step a, step b and step c to prepare the key intermediate compound of formula VII, carryin gout isomer resolution and protective group removal on the compound of formula VII to obtain a compound of formula XV, coupling the compound of formula XV with the compound of formula XIII, and salifying to form a target compound I. The preparation method has the advantages of substantial reduction of the production cost, simple production flow, yield increase, and suitableness for industrial production.
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Paragraph 0051-0055
(2019/02/26)
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- Palladium-catalyzed cyclization-Heck reaction of allenamides: An approach to 3-methylene-5-phenyl-1,2,3,4-tetrahydropyridine derivatives
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An efficient one-pot construction of functionalized 3-methylene-5-phenyl-1,2,3,4-tetrahydropyridine derivatives via palladium-catalyzed cyclization-Heck reaction of allenamides has been described. The 3-methylene-5-phenyl-1,2,3,4-tetrahydropyridine derivatives feature a nonconjugated diene, including one endo-enamine and one exocyclic double bond, which could be used for further transformation. Both aryl and vinyl halides performed very well under the standard conditions, delivering the corresponding products efficiently.
- Yan, Fachao,Liang, Hanbing,Song, Jian,Cui, Jie,Liu, Qing,Liu, Sheng,Wang, Ping,Dong, Yunhui,Liu, Hui
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- Three-membered fused ring substituted amino six-membered ring derivative and medicine applications thereof relates to a three-membered fused ring substituted amino six-membered ring derivative as shown in the general formula
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The present invention relates to a three-membered fused ring substituted amino six-membered ring derivative and medicine applications thereof, and more particularly to a three-membered fused ring substituted amino six-membered ring derivative as shown in the general formula (I) or a stereoisomer of the derivative, a pharmaceutically acceptable salt, a prodrug, a medicinal composition containing the derivative and an application of the derivative to preparation of the medicine, namely a dipeptidyl peptidase IV(DPP-IV) inhibitor, wherein the definitions of the various substituents in the general formula (I) are the same as those in the specification.
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Page/Page column 33; 34
(2017/08/02)
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- Stereoselective preparation of (1Z)- and (1E)-N-Boc-1-amino-1,3-dienes by stereospecific base-promoted 1,4-elimination
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The base-promoted 1,4-elimination reaction of N-Boc-1-amino-4-methoxy-2-alkene 1 is shown to proceed with perfect stereoselectivity to afford the corresponding N-Boc-1-amino-1,3-diene 2 in good yields. The reaction is highly stereospecific. The substrate
- Tayama, Eiji,Toma, Yuka
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p. 554 - 559
(2015/02/18)
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- DIHYDROPTERIDINONE DERIVATIVES, PREPARATION PROCESS AND PHARMACEUTICAL USE THEREOF
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Dihydroperidinone derivatives, preparation process and pharmaceutical use thereof are disclosed. Specially, new dihydroperidinone derivatives represented by general formula (I), wherein each substituent of the general formula (I) is defined as in the description, their preparation process, pharmaceutical compositions comprising said derivatives and their use as therapeutical agents, especially as Plk kinase inhibitors are disclosed.
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Page/Page column 30-31
(2012/08/08)
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- DIHYDROPTERIDINONE DERIVATIVES, PREPARATION PROCESS AND PHARMACEUTICAL USE THEREOF
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Dihydroperidinone derivatives, preparation process and pharmaceutical use thereof are disclosed. Specially, new dihydroperidinone derivatives represented by general formula (I), wherein each substituent of the general formula (I) is defined as in the description, their preparation process, pharmaceutical compositions comprising said derivatives and their use as therapeutical agents, especially as Plk kinase inhibitors are disclosed.
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- Evaluation of a 3-amino-8-azabicyclo[3.2.1]octane replacement in the CCR5 antagonist maraviroc
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The bicyclic 5-amino-3-azabicyclo[3.3.0]octanes were shown to be effective replacements for the 3-amino-8-azabicyclo[3.2.1]octane found in the CCR5 antagonist maraviroc.
- Lemoine, Rémy C.,Petersen, Ann C.,Setti, Lina,Baldinger, Thomas,Wanner, Jutta,Jekle, Andreas,Heilek, Gabrielle,deRosier, André,Ji, Changhua,Rotstein, David M.
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scheme or table
p. 1674 - 1676
(2010/07/03)
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- Optically active 1,4-dihydropyridine compounds as bradykinin antagonists
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This invention provides a compound of the formula (I): and its pharmaceutically acceptable salts, wherein A1 and A2 are each halo; R1 and R2 are independently C1-4 alkyl; R3 is substituted or unsubstituted, phenyl or naphthyl; Y is heterocyclic group sele
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- Synthesis of N-BOC-3-azabicyclo [3.3.0]octan-7-one via reductive Pauson-Khand cyclization and subsequent conversion to a novel diazatricyclic ring system
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An intramolecular reductive Pauson-Khand reaction of the hexacarbonyldicobalt complex of N-(tert-butyloxycarbonyl)allylpropargylamine under dry-state adsorption conditions directly afforded the saturated N-BOC-3-azabicyclo[3.3.0]octan-7-one when the react
- Becker, Daniel P.,Flynn, Daniel L.
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p. 5047 - 5054
(2007/10/02)
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- Studies of the solid-phase Pauson-Khand reaction: Selective in-situ enone reduction to 3-azabicyclo[3.3.0] octanones
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The Smit-Caple DSAC Pauson-Khand cyclization of a series of N-protected allyl propargyl amines in the absence of oxygen gave rise to formation of the saturated azabicyclo[3.3.0]octanones in excellent yields. Standard cyclization in air gave mixtures of sa
- Becker, Daniel P.,Flynn, Daniel L.
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p. 2087 - 2090
(2007/10/02)
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