- A very concise synthesis of a potent N-(1,3-thiazol-2-yl)pyridin-2-amine KDR kinase inhibitor
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A very concise synthesis of a potent KDR kinase inhibitor 1 is described. The synthesis features an exceedingly efficient one-pot preparation of the aminothiazole 6 followed by Pd-Xantphos catalyzed cross-coupling with chloropyridine aldehyde 11. Reductiv
- Zhao, Matthew,Yin, Jingjun,Huffman, Mark A.,McNamara, James M.
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Read Online
- Catalytic Decarboxylative C?N Formation to Generate Alkyl, Alkenyl, and Aryl Amines
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Transition-metal-catalyzed sp2 C?N bond formation is a reliable method for the synthesis of aryl amines. Catalytic sp3 C?N formation reactions have been reported occasionally, and methods that can realize both sp2 and sp3 C?N formation are relatively unexplored. Herein, we address this challenge with a method of catalytic decarboxylative C?N formation that proceeds through a cascade carboxylic acid activation, acyl azide formation, Curtius rearrangement and nucleophilic addition reaction. The reaction uses naturally abundant organic carboxylic acids as carbon sources, readily prepared azidoformates as the nitrogen sources, and 4-dimethylaminopyridine (DMAP) and Cu(OAc)2 as catalysts with as low as 0.1 mol % loading, providing protected alkyl, alkenyl and aryl amines in high yields with gaseous N2 and CO2 as the only byproducts. Examples are demonstrated of the late-stage functionalization of natural products and drug molecules, stereospecific synthesis of useful α-chiral alkyl amines, and rapid construction of different ureas and primary amines.
- Zhang, Yipin,Ge, Xia,Lu, Hongjian,Li, Guigen
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supporting information
p. 1845 - 1852
(2020/12/01)
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- The synthesis of phenyl carbamates catalyzed by iron (II) bromide: An oxidative approach for cross-coupling of phenols with formamides
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The carbamate group is a key structural motif in many approved drugs and pro-drugs. There is increasing use of carbamates in the medicinal chemistry and agrochemical industry. We present, reagents and chemical methodologies for the synthesis of carbamates, and recent applications. The direct coupling of simple phenols with mono- and di-alkyl formamides provided the phenylcarbamate products.
- Adurthi, Suryakumari,Sudhakar, Chithaluri,Vala, Manoj Kumar,Vanam, Shekhar
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- 1,2,4-TRIAZOLINOE CB1 INHIBITORS
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Disclosed are compounds according to Formula (I), and related pharmaceutical compositions. Also disclosed are therapeutic methods, e.g., of treating diseases such as diabetic kidney disease, diabetic nephropathy, obesity-related kidney disease, focal segmental glomerular sclerosis, IgA nephropathy, nephrotic syndrome, kidney fibrosis, Prader Willi syndrome, metabolic syndrome, gastrointestinal diseases, non-alcoholic liver disease, alcoholic liver disease, or non-alcoholic fatty liver disease, using the compounds of Formula (I).
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Page/Page column 45
(2021/09/11)
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- Highly efficient synthesis of hiv nnrti doravirine
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The development of an efficient and robust process for the production of HIV NNRTI doravirine is described. The synthesis features a continuous aldol reaction as part of a de novo synthesis of the key pyridone fragment. Conditions for the continuous flow aldol reaction were derived using microbatch snapshots of the flow process.
- Gauthier, Donald R.,Sherry, Benjamin D.,Cao, Yang,Journet, Michel,Humphrey, Guy,Itoh, Tetsuji,Mangion, Ian,Tschaen, David M.
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supporting information
p. 1353 - 1356
(2015/03/30)
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- PROCESS FOR MAKING REVERSE TRANSCRIPTASE INHIBITORS
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The present invention is directed to a novel process for synthesizing 3-(substituted phenoxy)-1-[(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl])-pyridin-2(1H)-one derivatives. The compounds synthesized by the processes of the invention are HIV reverse transcriptase inhibitors useful for inhibiting reverse transcriptase and HIV replication, and the treatment of human immunodeficiency virus infection in humans.
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Page/Page column 12; 13
(2015/06/18)
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- Ligand-assisted copper-catalyzed oxidative cross-coupling of simple phenols with formamides for the synthesis of carbamates
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An oxidative approach for the synthesis of phenyl carbamates has been achieved by ligand-assisted copper-catalyzed cross-dehydrogenative coupling (CDC) of phenols with formamides. The direct coupling of simple phenols with mono- and dialkyl formamides pro
- Reddy, Nagireddy Veera,Kumar, Gadde Sathish,Kumar, Pailla Santhosh,Kantam, M. Lakshmi,Reddy, Kallu Rajender
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supporting information
p. 2133 - 2138
(2014/11/08)
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- MONOCYCLIC PYRIDINE DERIVATIVE
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The present invention provides a novel compound having FGFR inhibitory activity or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition containing the same. Specifically, the present invention provides a compound represented by the following formula (I) or a pharmaceutically acceptable salt thereof: wherein n represents 0 to 2; A represents an arylene group or a heteroarylene group; G represents a single bond, an oxygen atom or —CH2—; E represents a nitrogen-containing non-aromatic heterocycle; R1 represents an alkoxy group or the like; R2 represents a hydrogen atom or the like; and R3 represents a hydrogen atom, an alkyl group, an alkoxy group or the like, with the proviso that when E represents an azetidine ring and R2 or R3 is present on a nitrogen atom on the azetidine ring, the R2 or R3 does not represent a hydrogen atom.
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Paragraph 0272; 0273; 0274
(2014/09/03)
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- PROCESS FOR MAKING REVERSE TRANSCRIPTASE INHIBITORS
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The present invention is directed to a novel process for synthesizing 3-(substituted phenoxy)-1-[(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl])-pyridin-2(1H)-one derivatives. The compounds synthesized by the processes of the invention are HIV reverse t
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(2014/06/24)
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- CHEMICAL COMPOUNDS
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In one aspect, the present invention relates to compounds of Formula (I): to pharmaceutically acceptable sa lts thereof, to methods of using them to treat bacterial infections, and to methods for their preparation.
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Page/Page column 132
(2009/03/07)
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- One-pot, three-step preparation of alkyl and aryl alkylcarbamates from S-methyl N-alkylthiocarbamates
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A general procedure for the synthesis of alkyl and aryl alkylcarbamates starting from the corresponding 5-methyl N-alkylthiocarbamates is described. This procedure consists of three steps that are carried out in a one-pot fashion, without isolating the intermediate N-alkylcarbamoyl chlorides or alkyl isocyanates. All the target products were obtained in high yields (16 examples, average yield 91%). To be noted is the recovery of a co-product of industrial interest, dimethyl disulfide, in a half mole amount for each mole of thiocarbamate, with complete exploitation of the reagent. The alkyl isocyanates, if required, can also be isolated in high yields. Georg Thieme Verlag Stuttgart.
- Artuso, Emma,Degani, Iacopo,Fochi, Rita,Magistris, Claudio
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experimental part
p. 1612 - 1618
(2009/04/03)
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- NOVEL THIOL DERIVATIVE, PROCESS FOR PRODUCING THE SAME AND USE THEREOF
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The present invention provides a novel thiol derivative [I] which has an excellent matrix metalloprotease inhibiting activity and is useful as a pharmaceutical composition, particularly a therapeutic agent or prophylactic agent for osteoarthritis and rheu
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- Concomitant Desulfurization and Transesterification of Alkyl Thionocarbamates
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Alkyl carbamate (such as 1) reacts with triphosgene at the nitrogen atom, whereas the analogous thionocarbamates (5) react at the sulfur. Subsequent treatment with various phenols or alcohols leads to the corresponding aryl carbamates or alkyl carbamates
- Joshi, Uday M.,Patkar, Laxmikant N.,Rajappa, Srinivasachari
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- Active salt forms with tyrosine kinase activity
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The present invention relates to orally active salt forms of the mesylate salt of 4-[2-(5-cyano-thiazol-2-ylamino)-pyridin-4-ylmethyl]-piperazine-1-carboxylic acid methylamide which inhibit, regulate and/or modulate tyrosine kinase signal transduction, compositions which contain these compounds, and methods of using them to treat tyrosine kinase-dependent diseases and conditions, such as angiogenesis, cancer, tumor growth, atherosclerosis, age related macular degeneration, diabetic retinopathy, retinal ischemia, macular edema, inflammatory diseases, and the like in mammals.
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Page/Page column 16
(2010/02/05)
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- Polymorphs with tyrosine kinase activity
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The present invention relates to active polymorphs of 4-[2-(5-cyano-thiazol-2-ylamino)-pyridin-4-ylmethyl]-piperazine-1-carboxylic acid methylamide which inhibit, regulate and/or modulate tyrosine kinase signal transduction, compositions which contain these compounds, and methods of using them to treat tyrosine kinase-dependent diseases and conditions, such as angio-genesis, cancer, tumor growth, atherosclerosis, age related macular degeneration, diabetic retinopathy, retinal ischemia, macular edema, inflammatory diseases, and the like in mammals.
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Page/Page column 16
(2010/02/05)
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- Salt forms with tyrosine kinase activity
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The present invention relates to salt forms of 4-[2-(5-cyano-thiazol-2-ylamino)-pyridin-4-ylmethyl]-piperazine-1-carboxylic acid methylamide which inhibit, regulate and/or modulate tyrosine kinase signal transduction, compositions which contain these compounds, and methods of using them to treat tyrosine kinase-dependent diseases and conditions, such as angio-genesis, cancer, tumor growth, atherosclerosis, age related macular degeneration, diabetic retinopathy, retinal ischemia, macular edema, inflammatory diseases, and the like in mammals.
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Page/Page column 18
(2010/02/05)
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- Nucleosides. Part LVI. Aminolysis of carbamates of adenosine and cytidine
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The 2-(4-nitrophenyl)ethoxycarbonyl (npeoc) group, introduced 1984 as protecting group for exocyclic amino functions of nucleic-acid bases, reacts with amines under mild conditions to urea derivatives. Treatment of 2',5'-di-O-acetyl-N6-[2-(4-nitrophenyl)ethoxycarbonyl]cordycepin (3) with NH3/MeOH overnight at room temperature affords cordycepin (4) and N6-carbamoylcordycepin (5). Preliminary investigations towards the elucidation of the reaction mechanism indicate that the aminolysis proceeds via an addition-elimination or an isocyanate mechanism, depending on the reaction conditions. The phenoxycarbonyl (phoc) group at N6 or N4 was chosen to study the mild conversion of carbamates with aromatic amines into ureas of adenosine and cytidine, respectively.
- Sigmund,Pfleiderer
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p. 1267 - 1280
(2007/10/02)
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- Transesterification of alkyl carbamate to aryl carbamate : Effect of varying the alkyl group
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Phosphorus oxychloride mediated transesterification of four alkyl N-methylcarbamates to several aryl N-methylcarbamates has been studied. Best yields are obtained from benzyl N-methylcarbamate.
- Deshpande, Sunita R.,Likhite, Anjali P.,Rajappa, Srinivasachari
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p. 10367 - 10370
(2007/10/02)
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- Contra-thermodynamic trans-esteripication of carbamates by counter-attack strategy: A viable non-phosgene, non-mic route to carbamate pesticides
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Treatment of methyl N-methylcarbaaate (1, R= Me) with phosphorus oxychloride and 1-naphthol results in the formation of the transesterified product, 1-naphthyl N-methylcarbamate (2, Ar=1-naphthy 1) in good yield. Similarly, ethyl N-methylthiocarbamate (5) is converted to 1-naphthyl N-methylcarbamate (2, Ar= 1-naphthyl) on treatment with phosphorus oxychloride and 1-naphthol. The mechanism of these interesting and industrially important transformations is discussed.
- Kulkarni,Naik,Tandel,Rajappa
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p. 1249 - 1256
(2007/10/02)
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- Phenyl carbamates
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O-Phenylcarbamates, e.g. those of the formula EQU1 are biocides, e.g. insecticides.
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