Month: November 2022

On March 5, 2020, Focken, Thilo; Andrez, Jean-Christophe; Burford, Kristen Nicole; Dehnhardt, Christoph Martin; Grimwood, Michael Edward; Jia, Qi; Lofstrand, Verner Alexander; Wilson, Michael Scott; Zenova, Alla Yurevna; Wesolowski, Steven Sigmund; Sun, Shaoyi published a patent.Electric Literature of 1261686-95-6 The title of the patent was Preparation of heteroaryl-substituted sulfonamide compounds and their use as sodium channel inhibitors. And the patent contained the following:

This invention is directed to pyridine- and thiophene-sulfonamide compounds of formula I, as stereoisomers, enantiomers, tautomers thereof or mixtures thereof; or pharmaceutically acceptable salts, solvates or prodrugs thereof, for the treatment of diseases or conditions associated with voltage-gated sodium channels, such as epilepsy and/ or epileptic seizure disorders. Compounds of formula I wherein A is (un)substituted pyridinediyl, (un)substituted thiophenediyl, (un)substituted thiazolediyl, etc.; R1 is (un)substituted aryl and (un)substituted (mono/bi)cyclic heteroaryl; R2 is (un)substituted 5- to 6-membered heteroaryl; R3 and R4 are independently H and alkyl; and individual stereoisomers, enantiomers, tautomers, mixtures, pharmaceutically acceptable salts, solvates and prodrugs thereof, are claimed. Example compound II was prepared by sulfamidation of 5,6-dichloropyridine-3-sulfonyl chloride with tert-Bu thiazol-4-ylcarbamate; the resulting tert-Bu ((5,6-dichloropyridin-3-yl)sulfonyl)(thiazol-4-yl)carbamate underwent amination with (S)-1-(5-chloro-2-fluorophenyl)ethan-1-amine hydrochloride to give tert-Bu (S)-((5-chloro-6-((1-(5-chloro-2-fluorophenyl)ethyl)amino)pyridin-3-yl)sulfonyl)(thiazol-4-yl)carbamate, which underwent hydrolysis to give compound II. The invention compounds were evaluated for their sodium channel inhibitory activity. From the assay, it was determined that compound II exhibited IC50 values of 2.820μM, 5.573μM and 5.003μM towards Nav1.6, Nav1.5 and Nav1.1, resp. The experimental process involved the reaction of 2-(Bromomethyl)-6-fluorobenzonitrile(cas: 1261686-95-6).Electric Literature of 1261686-95-6

The Article related to heteroaryl sulfonamide preparation sodium channel inhibitor, Heterocyclic Compounds (More Than One Hetero Atom): Thiazoles, Isothiazoles and other aspects.Electric Literature of 1261686-95-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On December 19, 2019, Focken, Thilo; Burford, Kristen Nicole; Lofstrand, Verner Alexander; Wilson, Michael Scott; Zenova, Alla Yurevna published a patent.Recommanded Product: 2-(Bromomethyl)-6-fluorobenzonitrile The title of the patent was Preparation of benzenesulfonamide compounds and their use as therapeutic agents. And the patent contained the following:

This invention is directed to benzenesulfonamide compounds of formula I, as stereoisomers, enantiomers, tautomers thereof or mixtures thereof; or pharmaceutically acceptable salts, solvates or prodrugs thereof, for the treatment of diseases or conditions associated with voltage-gated sodium channels (Nav1.6), such as epilepsy and/or epileptic seizure disorders. Compounds of formula I wherein m and n are independently 1 and 2; R1, R3a, R3b and each R4 are independently H and alkyl; R2 is thiazolyl, isothiazolyl and isoxazolyl; R5 is halo; each R6 is independently halo and alkoxy, provided that at least one R6 is alkoxy; R7 is azabicyclo[2.2.1]heptanylalkyl; R7 is ((methyl)(prop-2-yl)amino)alkyl when n is 2; and stereoisomers, enantiomers, tautomers, mixtures, pharmaceutically acceptable salts, solvates and prodrugs thereof, are claimed. Example compound II was prepared by a multistep procedure (procedure given). The invention compounds were evaluated for their voltage-gated sodium channel inhibitory activity. From the assay, it was determined that compound II exhibited IC50 values of 0.015 μM, > 30.00 μM and 9.603 μM towards Nav1.6, Nav1.5 and Nav1.1, resp. The experimental process involved the reaction of 2-(Bromomethyl)-6-fluorobenzonitrile(cas: 1261686-95-6).Recommanded Product: 2-(Bromomethyl)-6-fluorobenzonitrile

The Article related to benzenesulfonamide preparation voltage gated sodium channel inhibitor, Heterocyclic Compounds (More Than One Hetero Atom): Thiazoles, Isothiazoles and other aspects.Recommanded Product: 2-(Bromomethyl)-6-fluorobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On August 20, 2014, Han, Shiqing; Tong, Yao; Pan, Qiang; Jiang, Zengqiang; Miao, Dazhuang published a patent.COA of Formula: C7H3ClN2O2 The title of the patent was A synthetic method for 2-substituted benzothiazole derivatives. And the patent contained the following:

The invention relates to a process for the preparation of 2-substituted benzothiazole derivatives via heterocyclization of 2-halogenated nitrobenzene with elemental sulfur and aliphatic amines. For instance, 2-phenyl-benzothiazole was prepared from 1-chloro-2-nitrobenzene, sulfur, and benzylamine in 76% yield as a white solid. The experimental process involved the reaction of 3-Chloro-4-nitrobenzonitrile(cas: 34662-29-8).COA of Formula: C7H3ClN2O2

The Article related to benzothiazole preparation heterocyclization halonitrobenzene benzylamine sulfur, heterocyclization and other aspects.COA of Formula: C7H3ClN2O2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On April 30, 2003, Ali, Gameel A. M. El-Hag published an article.Name: 2-((1H-Indol-3-yl)methylene)malononitrile The title of the article was Studies on Thiazolopyridines. Part 3: Reactivity of Thiazolo[3,2-a]-3-aza[1,8]naphthyridine Towards Some Nucleophiles. And the article contained the following:

A variety of new thiazolo[3,2-a]pyridine derivatives having 3-indolyl group were produced by refluxing thiazolinone derivative with different benzylidenemalononitrile derivatives Reactivity of Thiazolo[3,2-a]-3-aza[1,8]naphthyridine (I) toward some nitrogen nucleophiles was investigated. Thus, the novel pyrazoles were obtained when I was allowed to react with hydrazine and Ph hydrazine in ethanol under reflux. On the other hand, pyrazolo[3′,4′:4,5]thiazolo[3,2-a]-3-aza[1,8]naphthyridine was formed by condensation of I with benzoyl hydrazine. Finally, condensed heterocyclic compounds containing pyran rings were obtained by treatment I with active ethylene compounds Antimicrobial activity of some of the product was also evaluated. The experimental process involved the reaction of 2-((1H-Indol-3-yl)methylene)malononitrile(cas: 75629-62-8).Name: 2-((1H-Indol-3-yl)methylene)malononitrile

The Article related to thiazolopyridine derivative preparation reactivity nucleophile antimicrobial activity, Heterocyclic Compounds (More Than One Hetero Atom): Thiazoles, Isothiazoles and other aspects.Name: 2-((1H-Indol-3-yl)methylene)malononitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Darmanin, Thierry; Godeau, Guihem; Guittard, Frederic; Klimareva, Elena L.; Schewtschenko, Irina; Perepichka, Igor F. published an article in 2018, the title of the article was A Templateless Electropolymerization Approach to Porous Hydrophobic Nanostructures Using 3,4-Phenylenedioxythiophene Monomers with Electron-Withdrawing Groups.Application In Synthesis of 3-Chloro-4-nitrobenzonitrile And the article contains the following content:

Controlling the surface structures of conducting polymers is extremely important for various applications not only because of their unique optoelectronic properties but also owing to the wetting properties of these materials. Using a templateless electropolymerization approach, we report the formation of porous polymer nanostructures from a series of 3,4-(1,2-phenylenedioxy)(PheDOT) derivatives with electron-withdrawing side groups (Cl, CN, CF, SOCH). In this templateless electropolymerization, trace water present in solution is sufficient to produce gas bubbles (O2 and H2) and, as a consequence, to form the porous nanostructures with a tendency to form nanotubes on the surface. We show that the substituents in PheDOT play an important role to control the porous nanostructures and, as a consequence, the surface hydrophobicity. Using 3,4-(1,3-propylenedioxy)type (ProDOT) derivative F4-BnDOT, the formation of densely packed nanofibers was demonstrated, and these are not a result of the presence of trace water. In this case, the surfaces are even more hydrophobic than for PheDOT-based polymers, displaying extremely high apparent water contact angles (θw = 138-144 °) and strong water adhesion. Such surfaces from electropolymerized conducting polymers could be used in a number of technol. applications, e.g. self-cleaning surfaces, micropatterning, water harvesting and microfluid systems. The experimental process involved the reaction of 3-Chloro-4-nitrobenzonitrile(cas: 34662-29-8).Application In Synthesis of 3-Chloro-4-nitrobenzonitrile

The Article related to phenylenedioxythiophene monomer derivative electron withdrawing group templateless electropolymerization property, Chemistry of Synthetic High Polymers: Ring-Opening and Other Polymerizations and other aspects.Application In Synthesis of 3-Chloro-4-nitrobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On May 5, 2016, Franconetti, A.; Dominguez-Rodriguez, P.; Lara-Garcia, D.; Prado-Gotor, R.; Cabrera-Escribano, F. published an article.Formula: C12H7N3 The title of the article was Native and modified chitosan-based hydrogels as green heterogeneous organocatalysts for imine-mediated Knoevenagel condensation. And the article contained the following:

A variety of methylenemalononitriles and Et cyanoacrylates derived from both aromatic and heteroaromatic aldehydes were synthesized by Knoevenagel condensation catalyzed with native and modified chitosan-based heterogeneous catalysts. The efficiency of our hydrogel organocatalysts, chitosan hydrogel beads and ureidyl-chitosan derivative hydrogel disks, was evaluated as function of pH, temperature and catalyst concentration by considering reaction rates, conversions, E/Z stereoselectivities, and kinetic studies of a model reaction between 4-nitrobenzaldehyde and Et cyanoacetate. An unprecedented study by solid state 13C CP MAS NMR of the employed catalyst when reaction was quenched after a 50% of conversion, has demonstrated that an imine-chitosan intermediate is formed during this process. Anal. of E/Z Et cyanoacrylate isomer mixtures for determining the corresponding stereoselectivity was carried out by NMR measuring carbon-proton coupling constants (3JC,H) using a novel CLIP-HSQMCB experiment Addnl., DFT calculations let us rationalize the observed E/Z stereoselectivities as well as to evaluate the role of ureidyl moiety on interaction with aldehydes and imine intermediate formation with chitosan derivative The experimental process involved the reaction of 2-((1H-Indol-3-yl)methylene)malononitrile(cas: 75629-62-8).Formula: C12H7N3

The Article related to aromatic aldehyde knoevenagel condensation chitosan hydrogel organocatalyst, Physical Organic Chemistry: Addition, Elimination, and Substitution Reactions and other aspects.Formula: C12H7N3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On July 31, 2008, Noritake, Shun; Shibata, Norio; Nakamura, Shuichi; Toru, Takeshi; Shiro, Motoo published an article.Application In Synthesis of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile The title of the article was Fluorinated Johnson reagent for transfer-trifluoromethylation to carbon nucleophiles. And the article contained the following:

A novel reagent, [(oxido)phenyl(trifluoromethyl)-λ4-sulfanylidene]dimethylammonium tetrafluoroborate has been developed for the electrophilic trifluoromethylation of carbon nucleophiles. The reagent was designed as a trifluorinated version of a Johnson-type methyl-transfer reagent. The first example of vinylogous trifluoromethylation of dicyanoalkylidenes is also demonstrated. The experimental process involved the reaction of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile(cas: 2510-01-2).Application In Synthesis of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile

The Article related to fluorinated johnson reagent transfer trifluoromethylation carbon nucleophile, Physical Organic Chemistry: Addition, Elimination, and Substitution Reactions and other aspects.Application In Synthesis of 2-(2,3-Dihydro-1H-inden-1-ylidene)malononitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On December 28, 2018, Bahuguna, Ashish; Kumar, Ashwani; Chhabra, Tripti; Kumar, Ajay; Krishnan, Venkata published an article.Name: 2-((1H-Indol-3-yl)methylene)malononitrile The title of the article was Potassium-Functionalized Graphitic Carbon Nitride Supported on Reduced Graphene Oxide as a Sustainable Catalyst for Knoevenagel Condensation. And the article contained the following:

A nanocomposite of potassium-functionalized graphitic carbon nitride (KGCN) and reduced graphene oxide (RGO) was fabricated by a facile hydrothermal method and used as a heterogeneous catalyst for Knoevenagel condensation and sustainable synthesis of aryl substituted chromenes. The prepared KGCN-RGO nanocomposite catalyst has been characterized by using various techniques, such as powder X-ray diffraction technique (PXRD), Fourier transform IR spectroscopy, SEM, transmission electron microscopy, thermogravimetric anal., and BET surface area anal. After detailed characterization, the nanocomposite was used as a heterogeneous catalyst to synthesize various aryl substituted chromenes in ethanol. The developed KGCN-RGO nanocatalyst also rendered good recyclability for the explored catalytic reactions. In addition, a high value of atom economy and a low value of E-factor are also key highlights of this green and sustainable catalytic protocol. The experimental process involved the reaction of 2-((1H-Indol-3-yl)methylene)malononitrile(cas: 75629-62-8).Name: 2-((1H-Indol-3-yl)methylene)malononitrile

The Article related to potassium functionalized graphitic carbon nitride knoevenagel condensation catalyst, Physical Organic Chemistry: Addition, Elimination, and Substitution Reactions and other aspects.Name: 2-((1H-Indol-3-yl)methylene)malononitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Armarego, Wilfred L. F. published an article in 1977, the title of the article was Pterins. Part 2. Stereochemistry of catalytic reduction of 6-methyl- and 6,7-dimethyl-pterin and of 2,4-diamino-6-methylpteridine.Category: nitriles-buliding-blocks And the article contains the following content:

Catalytic addition of 2 mols. of H to 7-deuterio-6-trideuteriomethylpterin gave a 0.8:1 mixture of cis- and trans-7-deuterio-6-trideuteriomethyl-5,6,7,8-tetrahydropterin. Similar reduction of 2,4-diamino-7-deuterio-6-(partial)trideuteriomethylpteridine gave a 1:1 mixture of cis- and trans-2,4-diamino-7-deuterio-6-(partial)trideuteriomethyl-5,6,7,8-tetrahydropteridine. However, catalytic reduction of 6,7-dimethyl- and 6,7-bis(trideuteriomethyl)pterin is stereospecific and gave only the cis 5,6,7,8-tetrahydro derivatives Reduction of 6,7-dimethylpterin with Na in EtOH gave a 1:1 mixture of cis- and trans-6,7-dimethyl-5,6,7,8-tetrahydropterin. The stereochem. of the products was deduced from 1H NMR spectroscopy. The experimental process involved the reaction of 2-Aminomalononitrile 4-methylbenzenesulfonate(cas: 5098-14-6).Category: nitriles-buliding-blocks

The Article related to catalyst reduction stereochem pterin, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines and other aspects.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On June 6, 1980, Taylor, Edward C.; Dumas, Donald J. published an article.HPLC of Formula: 5098-14-6 The title of the article was Pteridines. 47. Preparation and chemistry of 2-amino-6-carbalkoxy-3-cyano-5-substituted pyrazine 1-oxides: synthesis of pterin-6-carboxaldehyde. And the article contained the following:

A new procedure for the synthesis of 2-amino-3-cyano-5-substituted pyrazines I [R = CH(OMe)2, Me], useful intermediates for the synthesis of pteridines, is described. Oximation of β-oxo esters followed by reaction with aminomalononitrile provides 2-amino-6-carbalkoxy-3-cyano-5-substituted pyrazine 1-oxides II. Protection of the amino group as its (dimethylamino)methylenamino derivative I followed by SN2 decarbalkoxylation provides pyrazines, which on removal of the protecting group and deoxygenation give pyrazines III. This method is designed to be of use in cases where the β-oxo ester cannot be converted directly to the corresponding α-oxo aldoxime. The procedure is applied to the synthesis of III [R = CH(OMe)2], an intermediate in the synthesis of pterin-6-carboxaldehyde. The experimental process involved the reaction of 2-Aminomalononitrile 4-methylbenzenesulfonate(cas: 5098-14-6).HPLC of Formula: 5098-14-6

The Article related to pyrazine oxide amino cyano carbalkoxy, pterincarboxaldehyde, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines and other aspects.HPLC of Formula: 5098-14-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts