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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 12
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Original Articles

Efficient Large-Scale Synthesis of 2-Amino-5-methanesulfonylaminobenzenesulfonamide

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Pages 1909-1916 | Received 16 Jan 2008, Published online: 12 Jun 2008

REFERENCES

  • (a) Krueger , A. C. ; Madigan , D. L. ; Green , B. E. ; Hutchinson , D. K. ; Jiang , W. W. ; Kati , W. M. ; Liu , Y. ; Maring , C. J. ; Masse , S. V. ; McDaniel , K. F. ; Middleton , T. R. ; Mo , H. ; Molla , A. ; Montgomery , D. A. ; Ng , T. I. ; Kempf , D. J. Inhibitors of HCV NS5B polymerase: Synthesis and structure-activity relationships of unsymmetrical 1-hydroxy-4,4-dialkyl-3-oxo-3,4-dihydronaphthalenebenzothiadiazine derivatives . Bioorg. Med. Chem. Lett . 2007 , 17 , 2289 ; (b) Hutchinson , D. K. ; Bellettini , J. R. ; Betebenner , D. A. ; Bishop , R. D. ; Borchardt , T. B. ; Bosse , T. D. ; Cink , R. D. ; Flentge , C. A. ; Gates , B. D. ; Green , B. E. ; Hinmann , M. M. ; Huang , P. P. ; Klein , L. L. ; Krueger , A. C. ; Larson , D. P. ; Leanna , M. R. ; Liu , D. ; Madigan , D. L. ; McDaniel , K. F. ; Randolph , J. T. ; Rockway , T. W. ; Rosenberg , T. A. ; Stewart , K. D. ; Stoll , V. S. ; Wagner , R. ; Yeung , M. C. United States patent application 2005/0107364; file date, August 24, 2004; (c) Goldfarb , A. R. ; Berk , B. New Compounds. Derivatives of 2,5-diaminobenzenesulfonamide . J. Am. Chem. Soc . 1943 , 65 , 738 .
  • For other syntheses of N-(4-nitrophenyl)methanesulfonamide, see (a) Lee , J. ; Kang , S.-U. ; Kil , M.-J. ; Shin , M. ; Lim , J.-O. ; Choi , H.-K. ; Jin , M.-K. ; Kim , S. Y. ; Kim , S.-E. ; Lee , Y.-S. ; Min , K.-H. ; Kim , Y.-H. ; Ha , H.-J. ; Tran , R. ; Welter , J. D. ; Wang , Y. ; Szabo , T. ; Pearce , L. V. ; Lundberg , D. J. ; Toth , A. ; Pavlyukovets , V. A. ; Morgan , M. A. ; Blumberg , P. M. Analysis of structure-activity relationships for the `A-region' of N-(4-t-butylbenzyl)-Nα-[4-(methylsulfonylamino)benzyl]thiourea analogues as TRPV1 antagonists . Bioorg. Med. Chem. Lett . 2005 , 15 , 4136 ; (b) Kim , S. Y. ; Sung , N.-D. ; Choi , J. K. ; Kim , S. S. 1H-Benzotriazol-1-yl methanesulfonate: A regioselective N-mesylating reagent . Tetrahedron Lett . 1999 , 40 , 117 .
  • Girard , Y. ; Atkinson , J. G. ; Rokach , J. A new synthesis of 1,2,4-benzothiadiazines and a selective preparation of o-aminobenzenesulphonamides . J. Chem. Soc., Perkin Trans. 1 1979 , 1043 .
  • For other recent applications of this literature procedure to the synthesis of related 2-aminobenzenesulfonamides, see Rockway , T. W. ; Zhang , R. ; Liu , D. ; Betebenner , D. A. ; McDaniel , K. F. ; Pratt , J. K. ; Beno , D. ; Montgomery , D. ; Jiang , W. W. ; Masse , S. ; Kati , W. M. ; Middleton , T. ; Molla , A. ; Maring , C. J. ; Kempf , D. J. ; Inhibitors of HCV NS5B polymerase: Synthesis and structure-activity relationships of N-1-benzyl and N-1-[3-methylbutyl]-4-hydroxy-1,8-naphthyridon-3-yl benzothiadiazine analogs containing substituents on the aromatic ring . Bioorg. Med. Chem. Lett . 2006 , 16 , 3833 .

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