64910-52-7Relevant articles and documents
Reductive cyanation of organic chlorides using CO2 and NH3 via Triphos–Ni(I) species
Dong, Yanan,Li, Yuehui,Yang, Peiju,Zhao, Shizhen
, (2020/08/19)
Cyano-containing compounds constitute important pharmaceuticals, agrochemicals and organic materials. Traditional cyanation methods often rely on the use of toxic metal cyanides which have serious disposal, storage and transportation issues. Therefore, there is an increasing need to develop general and efficient catalytic methods for cyanide-free production of nitriles. Here we report the reductive cyanation of organic chlorides using CO2/NH3 as the electrophilic CN source. The use of tridentate phosphine ligand Triphos allows for the nickel-catalyzed cyanation of a broad array of aryl and aliphatic chlorides to produce the desired nitrile products in good yields, and with excellent functional group tolerance. Cheap and bench-stable urea was also shown as suitable CN source, suggesting promising application potential. Mechanistic studies imply that Triphos-Ni(I) species are responsible for the reductive C-C coupling approach involving isocyanate intermediates. This method expands the application potential of reductive cyanation in the synthesis of functionalized nitrile compounds under cyanide-free conditions, which is valuable for safe synthesis of (isotope-labeled) drugs.
Stereospecific copper-catalyzed domino ring opening and sp3 C-H functionalization of activated aziridines with N-alkylanilines
Sengoden, Mani,Bhowmick, Abhisikta,Punniyamurthy, Tharmalingam
supporting information, p. 158 - 161 (2017/11/27)
Copper efficiently catalyzed nucleophilic ring opening, sp3 C-H functionalization, and C-N bond formation in the presence of tert-butyl hydroperoxide to afford functionalized imidazolidines starting from N-sulfonylaziridines and Nalkylanilines. The products were obtained in high optical purities (95 → 99% ee) with excellent functional group tolerance.
3-CYANOANILINOALKYLARYLPIPERAZINE DERIVATIVE AND USE THEREOF IN PREPARING DRUGS
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Paragraph 0071; 0072, (2015/04/21)
Disclosed in the present invention is a 3-cyanoanilinoalkylarylpiperazine derivatives and use thereof in preparing drugs; the 3-cyanoanilinoalkylarylpiperazine derivatives disclosed by the present invention has very useful pharmaceutical properties and go
Highly specific N-monomethylation of primary aromatic amines
Le Pera, Adolfo,Leggio, Antonella,Liguori, Angelo
, p. 6100 - 6106 (2007/10/03)
A synthetic methodology for the specific conversion of primary aromatic amines into their N-monomethyl derivatives under very mild conditions is presented. Anilines are treated with 4-nitrobenzenesulfonyl (nosyl) chloride to generate the corresponding sulfonamides 2 in high yields. The subsequent N-methylation reaction of the sulfonamides 2 with a solution of diazomethane is rapid and quantitative. Removal of the nosyl protecting group is readily carried out using the reagent system mercaptoacetic acid/1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) affording the N-monomethylated aromatic amines 4. The procedure is convenient, efficient, and gives rise to the N-monomethyl-anilines exclusively.
3-AMIDINOANILINE DERIVATIVES, ACTIVATED BLOOD COAGULATION FACTOR X INHIBITORS, AND INTERMEDIATES FOR PRODUCING BOTH
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, (2008/06/13)
The present invention relates to a 3-amidinoaniline derivative represented by the general formula: wherein R represents a hydrogen atom, a lower alkyl group, a lower alkenyl group etc.; R1 represents a hydrogen atom, a hydroxy group, a lower alkyl group etc.; Y represents a single bond or an oxygen atom; and R2 represents a lower alkyl group or a group represented by the general formula: wherein n represents 1 or 2; and T represents a hydrogen atom or a group represented by the general formula:-C(=NH)-W wherein W represents a lower alkyl group; or a pharmaceutically acceptable salt thereof, which has a potent and selective activated blood coagulation factor X inhibitory activity, and an intermediate for producing both.
Anxiolytic activity of analogues of 4-benzylamino-2-methyl-7H- pyrrolo[2,3-d]pyrimidines
Meade, Eric A.,Sznaidman, Marcos,Pollard, Gerald T.,Beauchamp, Lilia M.,Howard, James L.
, p. 363 - 374 (2007/10/03)
An extensive series of analogues of the lead anxiolytic 4-benzylamino- 2-methylpyrrolo[2,3-d]pyrimidine 1 was synthesized and evaluated in the Geller-Seifter conflict test for anxiolytic activity to discover a less toxic derivative. Analysis of the SAR revealed that the most potent compounds were those with meta substituents on the benzylamino ring. In this group the most promising derivatives were 4-[bis(3,5-dimethylamino)]benzylamino-2-methyl- 7H-pyrrolo[2,3-d]pyrimidine 12 and 4-(3,5-dimethylbenzylamino)-2-methyl-7H- pyrrolo[2,3-d]pyrimidine 24. Potential metabolites of 12 were synthesized and checked for their anxiolytic activity. Less toxic analogues of the second lead 24 were prepared by extending the alkyl groups attached to the benzene ring moiety. The addition of a fluoro substituent to the benzene moiety in the extended alkyl chain analogue 4-(3,5-diethyl-2-fluorobenzylamino)2- methyl-7H-pyrrolo[2,3-d]pyrimidine 34 resulted in a compound with a longer duration of activity relative to its analogue 4-(3,5-diethylbenzylamino)-2- methyl-7H-pyrrolo[2,3-d]pyrimidine 26.
Synthesis of phenoxyacetic acid derivatives as highly potent antagonists of gastrin/cholecystokinin-B receptors. II
Takeda, Yasuyuki,Kawagoe, Keiichi,Yokomizo, Aki,Yokomizo, Yoshihiro,Hosokami, Toru,Shimoto, Yoshimasa,Tabuchi, Yoshiaki,Ogihara, Yoshiyasu,Otsubo, Rira,Honda, Yuko,Yokohama, Shuichi
, p. 951 - 961 (2007/10/03)
A series of phenoxyacetanilide derivatives was synthesized and their antagonist activities for human gastrin/cholecystokinin (CCK)-B and CCK-A receptors were evaluated. Among the compounds synthesized, 2-[3-[3-[N-[2-(N- methyl-N-phenylcarbamoylmethoxy)phe
