- Synthesis of various acylating agents directly from carboxylic acids
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A straightforward synthesis of acylating reagents such as Weinreb and MAP amides from aromatic, aliphatic carboxylic acids, and amino acids using PPh3/NBS combination is described. A chemo-selective modification of the carboxylic acid group into Weinreb amide in the presence of more reactive aldehydes and ketones is presented. All reactions were performed at ambient temperature under air using undried commercial grade solvent. Furthermore, the present methodology could be performed at a gram scale under inert-free reaction conditions. In addition, 7-azaindoline amide auxiliary (used for catalytic asymmetric aldol- and Mannich-type reactions), which behaves like Weinreb amide is also synthesized under similar reaction conditions.
- Pilathottathil, Fathima,Vineet Kumar, Doppalapudi,Kaliyamoorthy, Alagiri
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supporting information
p. 1622 - 1632
(2020/04/27)
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- Process for Making CGRP Receptor Antagonists
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The invention encompasses a novel process for making piperidinone carboxamide indane and azainane derivatives, which are CGRP receptor antagonists useful for the treatment of migraine.
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Paragraph 0203; 0204
(2016/06/01)
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- Iron-Catalyzed Michael Addition of Ketones to Polar Olefins
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The base metal complex tetrabutylammonium nitrosyltricarbonylferrate {Bu4N[Fe(CO)3(NO)] (TBA[Fe])} – catalyzes the conjugate addition of ketones to polar olefins. The reaction is applicable to a wide range of substrates leading to interesting building blocks for organic synthesis. Clear indications for an acid-base type rather than a C?H activation pathway exist. (Figure presented.).
- Zhang, Di-Han,Knelles, Jakob,Plietker, Bernd
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supporting information
p. 2469 - 2479
(2016/08/16)
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- Aerobic Asymmetric Dehydrogenative Cross-Coupling between Two C sp 3 -H Groups Catalyzed by a Chiral-at-Metal Rhodium Complex
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A sustainable C-C bond formation is merged with the catalytic asymmetric generation of one or two stereocenters. The introduced catalytic asymmetric cross-coupling of two Csp3-H groups with molecular oxygen as the oxidant profits from the oxidative robustness of a chiral-at-metal rhodium(III) catalyst and exploits an autoxidation mechanism or visible-light photosensitized oxidation. In the latter case, the catalyst serves a dual function, namely as a chiral Lewis acid for catalyzing enantioselective enolate chemistry and at the same time as a visible-light-driven photoredox catalyst. Green stuff: A sustainable C-C bond formation is merged with the catalytic asymmetric generation of one or two stereocenters by combining asymmetric enolate chemistry with either autoxidation or visible-light photosensitized oxidation. The robustness of a chiral-at-metal rhodium(III) catalyst serves to facilitate the reaction. PMP=para-methoxyphenyl, TFA=trifluoroacetic acid.
- Tan, Yuqi,Yuan, Wei,Gong, Lei,Meggers, Eric
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supporting information
p. 13045 - 13048
(2015/11/02)
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- PROCESS FOR MAKING CGRP RECEPTOR ANTAGONISTS
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The disclosure encompasses a novel process for making piperidinone carboxamide indane and azainane derivatives, having less steps and improved yields as compared to previous synthetic methods for making these compounds, which are CGRP receptor antagonists, useful for the treatment of migrane. Conditions for an amide bond formation between an acid and amine include for example reacting the compounds of Formulae B (after salt break) and C with an amide coupling reagent and optionally an additive and an acid and/or a base in a non-reactive solvent.
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Page/Page column 66
(2013/12/03)
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- 2-[(3a R,4 R,5 S,7a S)-5-{(1 S)-1-[3,5-bis(trifluoromethyl)phenyl]-2- hydroxyethoxy}-4-(2-methylphenyl)octahydro-2 H -isoindol-2-yl]-1,3-oxazol-4(5 H)-one: A potent human NK1 receptor antagonist with multiple clearance pathways
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Hydroisoindoline 2 has been previously identified as a potent, brain-penetrant NK1 receptor antagonist with a long duration of action and improved profile of CYP3A4 inhibition and induction compared to aprepitant. However, compound 2 is predict
- Kassick, Andrew J.,Jiang, Jinlong,Bunda, Jaime,Wilson, David,Bao, Jianming,Lu, Huagang,Lin, Peter,Ball, Richard G.,Doss, George A.,Tong, Xinchun,Tsao, Kwei-Lan C.,Wang, Hong,Chicchi, Gary,Karanam, Bindhu,Tschirret-Guth, Richard,Samuel, Koppara,Hora, Donald F.,Kumar, Sanjeev,Madeira, Maria,Eng, Waisi,Hargreaves, Richard,Purcell, Mona,Gantert, Liza,Cook, Jacquelyn,Devita, Robert J.,Mills, Sander G.
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p. 5940 - 5948
(2013/08/23)
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- Copper(II)-catalyzed meta-selective direct arylation of α-aryl carbonyl compounds
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Strong competition: A method for the meta-selective arylation of the highly versatile α-aryl carbonyl motif using diaryliodonium salts is described. In this CuII-catalyzed process the remote carbonyl group is capable of overpowering even strongly para-directing functionalities to form the elusive meta-products (see scheme). Remarkably, the arylation process can also operate under metal-free conditions.
- Duong, Hung A.,Gilligan, Ruth E.,Cooke, Michael L.,Phipps, Robert J.,Gaunt, Matthew J.
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p. 463 - 466
(2011/03/16)
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- Discovery of orally available 8-aza-5-thiaProstaglandin E1 analogs as highly selective EP4 agonists
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Analogs 8-aza-16-aryl prostaglandin E1 (PGE1) and 8-aza-5-thia-16-arylPGE1 were synthesized and evaluated with respect to their subtype receptor affinity and EP4 agonist activity for the purposes of identifying sub-type- selective EP
- Kambe, Tohru,Maruyama, Toru,Nakano, Masayuki,Yamaura, Yoshiyuki,Shono, Tomoyuki,Seki, Akiteru,Sakata, Kiyoto,Maruyama, Takayuki,Nakai, Hisao,Toda, Masaaki
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experimental part
p. 1523 - 1534
(2012/01/13)
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- NOVEL DIHYDROPYRIMIDIN-2(1H)-ONE COMPOUNDS AS S-NITROSOGLUTATHIONE REDUCTASE INHIBITORS
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The present invention is directed to novel dihydropyrimidin-2(1H)-one compounds useful as S-nitrosoglutathione reductase (GSNOR) inhibitors, pharmaceutical compositions comprising such compounds, and methods of making and using the same.
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Page/Page column 138-139
(2011/04/24)
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- TETRAHYDROISOQUINOLINE COMPOUND
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The present invention relates a specific tetrahydroisoquinoline compound which is useful as a chemokine receptor type 3 (CCR3) antagonist, and a pharmaceutical composition comprising the same as an active ingredient. The tetrahydroisoquinoline compound of the present invention is useful for the treatment or prevention of a disease in which CCR3 participates.
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Page/Page column 80
(2010/01/29)
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- HYDROXYMETHYL ETHER HYDROISOINDOLINE TACHYKININ RECEPTOR ANTAGONISTS
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The present invention is directed to certain hydroxymethyl ether hydroisoindoline compounds which are useful as neurokinin-1 (NK-1) receptor antagonists, and inhibitors of tachykinin and in particular substance P. The invention is also concerned with pharmaceutical formulations comprising these compounds as active ingredients and the use of the compounds and their formulations in the treatment of certain disorders, including emesis, urinary incontinence, LUTS, depression, and anxiety.
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Page/Page column 23
(2008/12/04)
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- HYDROISOINDOLINE TACHYKININ RECEPTOR ANTAGONISTS
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The present invention is directed to certain hydroisoindoline compounds which are useful as neurokinin-1 (NK-1) receptor antagonists, and inhibitors of tachykinin and in particular substance P. The invention is also concerned with pharmaceutical formulati
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Page/Page column 25
(2008/06/13)
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- Hydroisoindoline tachykinin receptor antagonists
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The present invention is directed to certain hydroisoindoline compounds which are useful as neurokinin-1 (NK-1) receptor antagonists, and inhibitors of tachykinin and in particular substance P. The invention is also concerned with pharmaceutical formulati
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Page/Page column 16
(2008/06/13)
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