Solvent- and Catalyst-Free Huisgen Cycloaddition to Rufinamide in Flow with a Greener, Less Expensive Dipolarophile

被引：48

作者：

Borukhova, Svetlana ^{[1
]}

Noel, Timothy ^{[1
]}

Metten, Bert ^{[2
]}

de Vos, Eric ^{[2
]}

Hessel, Volker ^{[1
]}

机构：

[1] Eindhoven Univ Technol, Dept Chem Engn & Chem Micro Flow Chem & Proc Tech, NL-5612 AZ Eindhoven, Netherlands

[2] SA Ajinomoto OmniChem NV, B-9230 Wetteren, Belgium

来源：

CHEMSUSCHEM | 2013年 / 6卷 / 12期

基金：

欧洲研究理事会;

关键词：

cycloaddition; green chemistry; microflow chemistry; novel process windows; solvent free; PROCESS DESIGN; PROCESS WINDOWS; DRUG DISCOVERY; COST-ANALYSIS; CHEMISTRY; MICROREACTOR;

D O I：

10.1002/cssc.201300684

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Give it a flow: A continuous-flow process for the synthesis of a 1,2,3-triazole precursor of Rufinamide has been developed. The protocol involves a solvent- and catalyst-free operation and utilizes reaction temperatures above the melting point of the target product to prevent microreactor clogging, resulting in a decrease of the operating time from hours to minutes. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：2220 / 2225

页数：6

共 48 条

[31] New Treatment Options for Lennox-Gastaut Syndrome [J].

Lemmon, Monica E. ;

Kossoff, Eric H. .

CURRENT TREATMENT OPTIONS IN NEUROLOGY, 2013, 15 (04) :519-528

[32] The use of atomic spectroscopy in the pharmaceutical industry for the determination of trace elements in pharmaceuticals [J].

Lewen, Nancy .

JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2011, 55 (04) :653-661

[33]

Maimone T. J., 2011, ANGEW CHEM, V123, P9062

[34] Continuous Flow Synthesis. A Pharma Perspective [J].

Malet-Sanz, Laia ;

Susanne, Flavien .

JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (09) :4062-4098

[35] An efficient synthesis of rufinamide, an antiepileptic drug [J].

Mudd, Whitney H. ;

Stevens, Erland P. .

TETRAHEDRON LETTERS, 2010, 51 (24) :3229-3231

[36] The role of flow in green chemistry and engineering [J].

Newman, Stephen G. ;

Jensen, Klavs F. .

GREEN CHEMISTRY, 2013, 15 (06) :1456-1472

[37] Cross-coupling in flow [J].

Noel, Timothy ;

Buchwald, Stephen L. .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5010-5029

[38] Accelerating Palladium-Catalyzed C-F Bond Formation: Use of a Microflow Packed-Bed Reactor [J].

Noel, Timothy ;

Maimone, Thomas J. ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (38) :8900-8903

[39] Palladium-catalyzed amination reactions in flow: overcoming the challenges of clogging via acoustic irradiation [J].

Noel, Timothy ;

Naber, John R. ;

Hartman, Ryan L. ;

McMullen, Jonathan P. ;

Jensen, Klavs F. ;

Buchwald, Stephen L. .

CHEMICAL SCIENCE, 2011, 2 (02) :287-290

[40]

Novartis A. G., 2000, U.S. Patent, Patent No. [6,156,907, 6156907]

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