- An efficient ruthenium(iv) catalyst for the selective hydration of nitriles to amides in water under mild conditions
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A Ru(iv) catalyst able to promote the selective hydration of nitriles to amides in water, at low metal loadings and under mild conditions, is presented. This journal is the Partner Organisations 2014.
- Tomás-Mendivil, Eder,Suárez, Francisco J.,Díez, Josefina,Cadierno, Victorio
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Read Online
- Hemilability-Driven Water Activation: A NiII Catalyst for Base-Free Hydration of Nitriles to Amides
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The NiII complex 1 containing pyridyl- and hydroxy-functionalized N-heterocyclic carbenes (NHCs) is synthesized and its catalytic utility for the selective nitrile hydration to the corresponding amide under base-free conditions is evaluated. The title compound exploits a hemilabile pyridyl unit to interact with a catalytically relevant water molecule through hydrogen-bonding and promotes a nucleophilic water attack to the nitrile. A wide variety of nitriles is hydrated to the corresponding amides including the pharmaceutical drugs rufinamide, Rifater, and piracetam. Synthetically challenging α-hydroxyamides are accessed from cyanohydrins under neutral conditions. Related catalysts that lack the pyridyl unit (i.e., compounds 2 and 4) are not active whereas those containing both the pyridyl and the hydroxy or only the pyridyl pendant (i.e., compounds 1 and 3) show substantial activity. The linkage isomer 1′ where the hydroxy group is bound to the metal instead of the pyridyl group was isolated under different crystallization conditions insinuating a ligand hemilabile behavior. Additional pKa measurements reveal an accessible pyridyl unit under the catalytic conditions. Kinetic studies support a ligand-promoted nucleophilic water addition to a metal-bound nitrile group. This work reports a Ni-based catalyst that exhibits functional hemilability for hydration chemistry.
- Singh, Kuldeep,Sarbajna, Abir,Dutta, Indranil,Pandey, Pragati,Bera, Jitendra K.
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- An efficient synthesis of rufinamide, an antiepileptic drug
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A two-step, one-pot synthesis of rufinamide, an antiepileptic drug, has been developed. 2,6-Difluorobenzyl azide reacts with methyl 3-methoxyacrylate followed by methanolic ammonia to afford rufinamide in 89% yield. The new method generates less waste and uses reagents that are both less expensive and less toxic than other reported syntheses.
- Mudd, Whitney H.,Stevens, Erland P.
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- Photoredox Catalysis at Copper(II) on Chitosan: Application to Photolatent CuAAC
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In this article we report the first example of a heterogeneous photolatent catalyst for the copper-catalyzed azide-alkyne cycloaddition (CuAAC) that is supported on chitosan. The heterogeneous copper(II) precatalyst was easily prepared by reaction of [Cu
- Jennah, Oumayma,Beniazza, Redouane,Lozach, Cédric,Jardel, Damien,Molton, Florian,Duboc, Carole,Buffeteau, Thierry,El Kadib, Abdelkrim,Lastécouères, Dominique,Lahcini, Mohammed,Vincent, Jean-Marc
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Read Online
- Novel Cu(I)-catalyzed one-pot multicomponent synthesis of the antiepileptic drug rufinamide
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Abstract: This work represents a new synthesis of the antiepileptic drug rufinamide, through a one-pot multicomponent approach employing a Cu(I) as a catalyst. In this methodology, 2,6-difluoro benzyl bromide reacts with NaN3 and propiolamide i
- Meena,Rao, R. Nishanth,Maiti, Barnali,Chanda, Kaushik
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Read Online
- Continuous flow total synthesis of rufinamide
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Small molecules bearing 1,2,3-triazole functionalities are important intermediates and pharmaceuticals. Common methods to access the triazole moiety generally require the generation and isolation of organic azide intermediates. Continuous flow synthesis provides the opportunity to synthesize and consume the energetic organoazides, without accumulation thereof. In this report, we described a continuous synthesis of the antiseizure medication rufinamide. This route is convergent and features copper tubing reactor-catalyzed cycloaddition reaction. Each of the three chemical steps enjoys significant benefits and has several advantages by being conducted in flow. The total average residence time of the synthesis is approximately 11 min, and rufinamide is obtained in 92% overall yield.
- Zhang, Ping,Russell, M. Grace,Jamison, Timothy F.
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Read Online
- Aerobic oxidation of primary amines to amides catalyzed by an annulated mesoionic carbene (MIC) stabilized Ru complex
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Catalytic aerobic oxidation of primary amines to the amides, using the precatalyst [Ru(COD)(L1)Br2] (1) bearing an annulated π-conjugated imidazo[1,2-a][1,8]naphthyridine-based mesoionic carbene ligand L1, is disclosed. This catalytic protocol is distinguished by its high activity and selectivity, wide substrate scope and modest reaction conditions. A variety of primary amines, RCH2NH2 (R = aliphatic, aromatic and heteroaromatic), are converted to the corresponding amides using ambient air as an oxidant in the presence of a sub-stoichiometric amount of KOtBu in tBuOH. A set of control experiments, Hammett relationships, kinetic studies and DFT calculations are undertaken to divulge mechanistic details of the amine oxidation using 1. The catalytic reaction involves abstraction of two amine protons and two benzylic hydrogen atoms of the metal-bound primary amine by the oxo and hydroxo ligands, respectively. A β-hydride transfer step for the benzylic C-H bond cleavage is not supported by Hammett studies. The nitrile generated by the catalytic oxidation undergoes hydration to afford the amide as the final product. This journal is
- Yadav, Suman,Reshi, Noor U Din,Pal, Saikat,Bera, Jitendra K.
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p. 7018 - 7028
(2021/11/17)
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- Mechanochemical Synthesis of Primary Amides
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Ball milling of aromatic, heteroaromatic, vinylic, and aliphatic esters with ethanol and calcium nitride afforded the corresponding primary amides in a transformation that was compatible with a variety of functional groups and maintained the integrity of a stereocenter α to carbonyl. This methodology was applied to α-amino esters and N-BOC dipeptide esters and also to the synthesis of rufinamide, an antiepileptic drug.
- Gómez-Carpintero, Jorge,Sánchez, J. Domingo,González, J. Francisco,Menéndez, J. Carlos
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p. 14232 - 14237
(2021/10/20)
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- Continuous synthesis method of lulaninamide
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The invention provides a continuous rufinamide synthesizing method. The continuous rufinamide synthesizing method comprises, with existence of acid-binding agent, continuously inputting 1, 2, 3-triazole-4-methyl carboxylate and 2, 6-difluorobenzyl chloride into a first continuous reaction device for continuous condensation reaction to obtain continuous condensation products, and continuously discharging the continuous condensation products; continuously inputting the continuous condensation products and ammonia gas or ammonia-containing solution into a second continuous reaction device for ammonolysis reaction to obtain rufinamide, and continuously discharging the rufinamide. The continuous rufinamide synthesizing method not only avoids production of isomers during cyclization of conventional routes to simplify the purification process of finished products, but also effectively reduces the process costs and shortens the reaction route; meanwhile, compared with batch equipment, the continuous rufinamide synthesizing method is implemented in a continuous reaction device; due to the facts the reaction system is small and heat exchange speed is high, reaction conditions can be more intense but safer.
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Paragraph 0048-0087
(2020/11/11)
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- Sequencing [3+2]-cycloaddition and multicomponent reactions: A regioselective microwave-assisted synthesis of 1,4-disubstituted 1,2,3-triazoles using ionic liquid supported Cu(II) precatalysts in methanol
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Heterocyclic compounds with two to three nitrogen atoms play a pivotal role in the normal life cycle of a cell. Further the design and synthesis of a quality heterocyclic compound library with N-atoms as new chemical probes active, is vital in drug discov
- Saikia, Ananya Anubhav,Nishanth Rao,Das, Soumyadip,Jena, Sushovan,Rej, Sourav,Maiti, Barnali,Chanda, Kaushik
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- Highly regioselective and sustainable solar click reaction: A new post-synthetic modified triazole organic polymer as a recyclable photocatalyst for regioselective azide-alkyne cycloaddition reaction
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The synthesis of pharmaceutically active 1,2,3-triazoles has been continuously scrutinized in the search for unique and effective catalysts to make the process efficient, green, and sustainable. Here, we are presenting a new visible light active Ni(ii) cyclam-integrated triazole-linked organic polymer (Ni-TLOP) photocatalyst for the synthesis of 1,2,3-triazole compounds with excellent efficiency and regioselectivity. The reaction was studied for a series of substrates and the absolute regioselectivity of a representative triazole product has also been confirmed by X-ray crystallography. The proficiency and chemical orthogonality of the Ni-TLOP are remarkable and it shows enhanced efficiency and regioselectivity. The use of a recyclable photocatalyst and non-hazardous reagents makes the catalytic system sustainable and environmentally friendly. This photocatalyzed click reaction technique has been successfully applied to the expedient synthesis of one of the most sold anti-epileptic drugs rufinamide.
- Yadav, Dolly,Singh, Nem,Kim, Tae Wu,Kim, Jae Young,Park, No-Joong,Baeg, Jin-Ook
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supporting information
p. 2677 - 2685
(2019/06/13)
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- Organic synthesis in a modular robotic system driven by a chemical programming language
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The synthesis of complex organic compounds is largely a manual process that is often incompletely documented. To address these shortcomings, we developed an abstraction that maps commonly reported methodological instructions into discrete steps amenable to automation. These unit operations were implemented in a modular robotic platform by using a chemical programming language that formalizes and controls the assembly of the molecules. We validated the concept by directing the automated system to synthesize three pharmaceutical compounds, diphenhydramine hydrochloride, rufinamide, and sildenafil, without any human intervention. Yields and purities of products and intermediates were comparable to or better than those achieved manually. The syntheses are captured as digital code that can be published, versioned, and transferred flexibly between platforms with no modification, thereby greatly enhancing reproducibility and reliable access to complex molecules.
- Steiner, Sebastian,Wolf, Jakob,Glatzel, Stefan,Andreou, Anna,Granda, Jaros?aw M.,Keenan, Graham,Hinkley, Trevor,Aragon-Camarasa, Gerardo,Kitson, Philip J.,Angelone, Davide,Cronin, Leroy
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- Bifunctional organometallic catalysts for selective hydration of nitriles to amides
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In this report, we highlight our recent contributions towards the development of bifunctional catalysts for selective hydration of nitriles to amides.
- Singh, Kuldeep,Sarbajna, Abir,Bera, Jitendra K.
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p. 853 - 861
(2020/06/26)
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- A multi-substituted three nitrogen zole derivatives preparation method (by machine translation)
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The present invention discloses a multi-substituted three nitrogen zole derivatives of the preparation method, comprises the following steps: the acrolein or acrolein derivatives, the corresponding azide compound or azido derivatives, strong acid and solv
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Paragraph 0034-0037
(2019/01/14)
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- Bis(allyl)-ruthenium(IV) complexes with phosphinous acid ligands as catalysts for nitrile hydration reactions
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Several mononuclear ruthenium(iv) complexes with phosphinous acid ligands [RuCl2(η3:η3-C10H16)(PR2OH)] have been synthesized (78-86% yield) by treatment of the dimeric precursor [{RuCl(μ-Cl)(η3:η3-C10H16)}2] (C10H16 = 2,7-dimethylocta-2,6-diene-1,8-diyl) with 2 equivalents of different aromatic, heteroaromatic and aliphatic secondary phosphine oxides R2P(O)H. The compounds [RuCl2(η3:η3-C10H16)(PR2OH)] could also be prepared, in similar yields, by hydrolysis of the P-Cl bond in the corresponding chlorophosphine-Ru(iv) derivatives [RuCl2(η3:η3-C10H16)(PR2Cl)]. In addition to NMR and IR data, the X-ray crystal structures of representative examples are discussed. Moreover, the catalytic behaviour of complexes [RuCl2(η3:η3-C10H16)(PR2OH)] has been investigated for the selective hydration of organonitriles in water. The best results were achieved with the complex [RuCl2(η3:η3-C10H16)(PMe2OH)], which proved to be active under mild conditions (60 °C), with low metal loadings (1 mol%), and showing good functional group tolerance.
- Tomás-Mendivil, Eder,Francos, Javier,González-Fernández, Rebeca,González-Liste, Pedro J.,Borge, Javier,Cadierno, Victorio
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p. 13590 - 13603
(2016/09/04)
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- Benzylic C-H Azidation Using the Zhdankin Reagent and a Copper Photoredox Catalyst
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An azidation method for C-N bond formation at benzylic C-H positions is described using copper-catalyzed visible light photochemistry and the Zhdankin azidoiodinane reagent. The method is applicable to a wide range of substrates bearing different functional groups and having a primary, secondary, or tertiary benzylic position, and is thought to proceed through a radical chain reaction.
- Rabet, Pauline T. G.,Fumagalli, Gabriele,Boyd, Scott,Greaney, Michael F.
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supporting information
p. 1646 - 1649
(2016/04/26)
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- New solventless and metal-free synthesis of the antiepileptic drug 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide (Rufinamide) and analogues
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This work presents a new synthesis of the antiepileptic drug rufinamide - 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide) in chemical form - and some analogue compounds, through a one-pot reaction employing a solventless, metal-free catalysis and without any reducing reagent. The great novelty presented is the synthesis of 4-trichloroacetyl-1-(2,6-difluorobenzyl/benzyl/4-methoxybenzyl)-5-methyl(phenyl)-1H-1,2,3-triazoles as new precursors from a regioselective 1,3-dipolar cycloaddition reaction between 1,1,1-trichloro-4-alkoxyalk-3-en-2-ones and some benzyl azides, which are converted into rufinamide and the analogues by an addition-elimination reaction with an aqueous solution of NH4OH in good yields (42-52%).
- Bonacorso, Helio G.,Moraes, Maiara C.,Luz, Fábio M.,Quintana, Pedro S.,Zanatta, Nilo,Martins, Marcos A.P.
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p. 441 - 444
(2015/04/27)
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- Direct access to 1,4-disubstituted 1,2,3-triazoles through organocatalytic 1,3-dipolar cycloaddition reaction of α,β-unsaturated esters with azides
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DBU-catalyzed organocatalytic 1,3-dipolar cycloaddition reactions of α,β-unsaturated esters with azides have been developed. This strategy generates 1,4-disubstituted 1,2,3-triazoles in high yields with high regioselectivities. It is demonstrated that some of these products can be transformed into important pharmaceutical agents.
- Li, Wenjun,Zhou, Xiao,Luan, Yepeng,Wang, Jian
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p. 88816 - 88820
(2015/11/09)
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- Exploring rhodium(I) complexes [RhCl(COD)(PR3)] (COD = 1,5-cyclooctadiene) as catalysts for nitrile hydration reactions in water: The aminophosphines make the difference
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Several rhodium(I) complexes, [RhCl(COD)(PR3)], containing potentially cooperative phosphine ligands, have been synthesized and evaluated as catalysts for the selective hydration of organonitriles into amides in water. Among the different phosphines screened, those of general composition P(NR 2)3 led to the best results. In particular, complex [RhCl(COD){P(NMe2)3}] was able to promote the selective hydration of a large range of nitriles in water without the assistance of any additive, showing a particularly high activity with heteroaromatic and heteroaliphatic substrates. Employing this catalyst, the antiepileptic drug rufinamide was synthesized in high yield by hydration of 4-cyano-1-(2,6- difluorobenzyl)-1H-1,2,3-triazole. For this particular transformation, complex [RhCl(COD){P(NMe2)3}] resulted more effective than related ruthenium catalysts.
- Tomas-Mendivil, Eder,Garcia-Alvarez, Rocio,Vidal, Cristian,Crochet, Pascale,Cadierno, Victorio
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p. 1901 - 1910
(2014/06/24)
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- PROCESS FOR PREPARATION OF 1,2,3-TRIAZOLE-4 CARBOXAMIDES
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The invention relates to the preparation of 1,2,3-triazole-4-carboxamide of general Formula I: wherein R1 and R2 may be the same or different and are selected from H, F, Cl, Br, I, OR, C(O)R, NH2, NHR or NR2. R can be a linear or branched alkyl group, for example a C1-C4 alkyl group. In exemplary embodiments, R1 and R2 are independently selected from H, F, Cl, Br, and I. The compound of Formula I can be Rufinamide.
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Paragraph 0064
(2014/06/23)
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- A PROCESS FOR PREPARING TRIAZOLE COMPOUNDS
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The present invention relates to process for preparing triazole compounds used in the treatment of epilepsy. The process comprises of reacting compound of 2, 6 difluoroazide (II) with 2, 3 dihalo compound (III) to form compound of formula I, which on further treatment with an aminating agent gives Rufinamide (IV). 2, 6 difluoroazide (II) is reacted with 2, 3 dihalo compound (III) in the presence of a solvent. The reaction can be carried out in a single pot without isolation of intermediates.
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(2014/05/24)
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- A PROCESS FOR THE PREPARATION OF RUFINAMIDE AND INTERMEDIATES THEREOF
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Provided are processes for the preparation of rutinamide and compounds which are intermediate compounds used in the processes for the preparation of rutinamide. Rutinamide is an anticonvulsant drug that is used in combination with other antiepileptic medicaments for the treatment of a rare form of epilepsy, Lennox-Gastaut syndrome. Formula (I)
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Page/Page column 25
(2014/08/20)
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- RUFINAMIDE SOLID DISPERSION
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The present invention provides a solid dispersion of rufinamide in combination with a pharmaceutically acceptable carrier, process for its preparation and pharmaceutical compositions comprising it.
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Page/Page column 5
(2014/02/15)
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- PROCESS FOR PREPARATION OF RUFINAMIDE
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The present invention relates to a novel process for preparation of rufinamide (I) comprising: reacting 2,6-difluorobenzyl azide (II) and propiolic acid (III) in a mixture of alcohol and water to produce 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid (IV), esterifying the acid (IV) to ester (V) and treating ester (V) with ammonia. The invention further relates to process for purification of 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid (IV), by crystallization from a mixture of alcohol and water. The present invention also provides process for purification of rufinamide (I) by crystallization from mixture of polar aprotic solvent with water or alcohol.
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Paragraph 0040
(2014/12/09)
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- Facet-dependent catalytic activity of Cu2O nanocrystals in the one-pot synthesis of 1,2,3-triazoles by multicomponent click reactions
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We report the highly facet-dependent catalytic activity of Cu2O nanocubes, octahedra, and rhombic dodecahedra for the multicomponent direct synthesis of 1,2,3-triazoles from the reaction of alkynes, organic halides, and NaN3. The catalytic activities of clean surfactant-removed Cu 2O nanocrystals with the same total surface area were compared. Rhombic dodecahedral Cu2O nanocrystals bounded by {110} facets were much more catalytically active than Cu2O octahedra exposing {111} facets, whereas Cu2O nanocubes displayed the slowest catalytic activity. The superior catalytic activity of Cu2O rhombic dodecahedra is attributed to the fully exposed surface Cu atoms on the {110} facet. A large series of 1,4-disubstituted 1,2,3-triazoles have been synthesized in excellent yields with high regioselectivity under green conditions by using these rhombic dodecahedral Cu2O catalysts, including the synthesis of rufinamide, an antiepileptic drug, demonstrating the potential of these nanocrystals as promising heterogeneous catalysts for other important coupling reactions.
- Chanda, Kaushik,Rej, Sourav,Huang, Michael H.
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p. 16036 - 16043
(2014/04/03)
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- PROCESS FOR PREPARATION OF RUFINAMIDE
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The invention relates to a novel, industrially viable, cost effective process for the preparation of 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide commonly known as Rufinamide and intermediates thereof.
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Paragraph 0031
(2013/07/25)
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- Safe and highly efficient syntheses of triazole drugs using Cu2O nanoparticle in aqueous solutions
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Triazole moiety is frequently employed in drug discovery and optimization. However, most syntheses of triazole drugs involve isolation of highly explosive azides. Herein we report safe and high efficient syntheses of triazole drugs in aqueous/organic solvent systems with Cu2O nanoparticle (Cu 2O-NP) as the catalyst of azide-alkyne cycloaddition (CuAAC). Since Cu2O-NP can be efficiently dispensed in aqueous and some organic solvents, the azide solutions from the previous preparation could be used directly in the next CuAAC stage without isolation. Therefore, this synthetic strategy is safe, convenient, and high yielding for the syntheses of triazole drugs.
- Wang, Jing-Han,Pan, Cheng-Wen,Li, Yong-Tao,Meng, Fan-Fei,Zhou, Hong-Gang,Yang, Cheng,Zhang, Quan,Bai, Cui-Gai,Chen, Yue
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p. 3406 - 3409
(2013/07/19)
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- PROCESS FOR PREPARATION OF RUFINAMIDE
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The present invention relates to a novel process for preparation of rufinamide (I) comprising: reacting 2,6-difluorobenzyl azide (II) and propiolic acid (III) in a mixture of alcohol and water to produce 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxyl
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- IMPROVED PROCESS FOR THE PREPARATION OF RUFINAMIDE
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The invention relates to a novel, industrially viable, cost effective process for the preparation of 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide commonly known as Rufinamide and intermediates thereof.
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Page/Page column 10
(2012/03/26)
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- PROCESS FOR PREPARATION OF FLUORINATED TRIAZOLE COMPOUND
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The present invention discloses a process for the preparation of 1-[(2,6-difluorophenyl)methyl]-1H-1,2,3-triazole-4-carboxamide of Formula (I), comprising regioselective cycloaddition of 2,6-difluorobenzyl halide of Formula (II), wherein X is chloride, br
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Page/Page column 16
(2012/03/27)
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- Polymorph of rufinamide and process for obtaining it
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The present invention refers to a new polymorph of Rufinamide, designed as Form R-5, the process for obtaining it, the composition containing it and its use as medicament. The new polymorph of Rufinamide shows good stability and appropriate physico-chemic
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Page/Page column 7
(2012/06/30)
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- IMPROVED PROCESS FOR PREPARING RUFINAMIDE INTERMEDIATE
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The present invention refers to an improved method for the preparation of compound 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid substantially free of its 3H-I isomer. The invention also refers to the use of said intermediate for the preparation of Rufinamide and for obtaining a new polymorphic form of Rufinamide, designed as Form R-5. The invention also refers to said new polymorph of Rufinamide, and to the composition containing it and its use as medicament. The new polymorph of Rufinamide shows good stability and appropriate physico-chemical properties for its manipulation on industrial scale. Polymorph Form R-5 will be suitable to use as pharmaceutical for the treatment of convulsions, especially for the treatment of epilepsy.
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- Crystalline forms of rufinamide
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Disclosed is a crystalline form of rufinamide selected from: ? a substantially anhydrous and approximately monosolvated with trifluoroacetic acid crystalline form, hereinafter designated as Form a, and ? a crystalline form, hereinafter designated as Form β, characterised by an XRPD spectrum as shown in Figure 3, wherein the most intense peaks fall at 4.5, 9.0, 13.5, 18.0, 18.8, 19.5, 20.6, 24.6, 25.7, 26.5, 27.4, 27.9, 28.7, 30.0 and 31.8 ± 0.2° in 2θ.
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Page/Page column 5
(2011/04/18)
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- CRYSTALLINE FORMS OF RUFINAMIDE
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Disclosed is a crystalline form of rufinamide selected from: a substantially anhydrous and approximately monosolvated with trifluoroacetic acid crystalline form, hereinafter designated as Form α, anda crystalline form, hereinafter designated as Form β, characterised by an XRPD spectrum as shown in FIG. 3, wherein the most intense peaks fall at 4.5, 9.0, 13.5, 18.0, 18.8, 19.5, 20.6, 24.6, 25.7, 26.5, 27.4, 27.9, 28.7, 30.0 and 31.8±0.2° in 2θ.
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Page/Page column 2
(2011/02/26)
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- METHOD FOR THE PREPARATION OF RUFINAMIDE
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The invention provides a novel process for the regioselective preparation of a compound of formula (I)
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Page/Page column 3
(2010/09/18)
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- Process for the preparation of rufinamide
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The invention provides a novel process for the regioselective preparation of a compound of formula (I)
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Page/Page column 6
(2010/10/03)
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- PROCESS FOR THE PREPARATION OF RUFINAMIDE
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The present invention relates to a process for the preparation of rufinamide of formula (I), which process comprises: (i) reacting a 2,6-difluorobenzylhaIide of formula (II), wherein X is chloride, bromide or iodide, with an azide to obtain 2-(azidomethyl)-1,3- difluorobenzene of formula (III); (ii) reacting 2-(azidomethyl)-1,3-difluorobenzene of formula (III) with methyl propiolate to obtain methyl 1-(2,6-difluorobenzyl)-1 H-1,2,3- triazole-4-carboxylic acid of formula (IV); and (iii) reacting methyl 1-(2,6-difluorobenzyl)- 1 H-1,2,3-triazole-4-carboxylic acid of formula (IV) with ammonia to obtain rufinamide of formula (I).
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Page/Page column 13-14
(2010/04/30)
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- Process for preparing 1-substituted 4-cyano-1,2,3-triazoles
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PCT No. PCT/EP97/03671 Sec. 371 Date Jan. 8, 1999 Sec. 102(e) Date Jan. 8, 1999 PCT Filed Jul. 10, 1997 PCT Pub. No. WO98/02423 PCT Pub. Date Jan. 22, 1998The invention relates on the one hand to a novel preparation of compounds of the formula (I) in whic
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- Aralkyltriazole compounds
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1-phenyl-lower alkyl-1H-1,2,3-triazole compounds of the formula STR1 in which Ph represents phenyl substituted by up to and including 3 substituents selected from lower alkyl, halogen and trifluoromethyl, alk represents lower alkylidene, and wherein either R1 represents hydrogen, lower alkyl, lower alkoxy, amino, N-lower alkylamino, N,N-di-lower alkylamino, N-lower alkanoylamino, carbamoyl, N-lower alkanoylcarbamoyl, N-lower alkylcarbamoyl or N,N-di-lower alkylcarbamoyl and R2 represents carbamoyl, N-lower alkanoylcarbamoyl, N-lower alkylcarbamoyl or N,N-di-lower alkylcarbamoyl or R1 represents carbamoyl, N-lower alkanoylcarbamoyl, N-lower alkylcarbamoyl or N,N-di-lower alkylcarbamoyl and R2 represents hydrogen or lower alkyl, have anti-convulsive properties and can be used as medicaments.
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