Solid phase synthesis of substituted aminosulfonyl ureas using a sulfonylcarbamate linker

Tetrahedron Letters

Volumn 38, Issue 43, 1997, Pages 7479-7482

  Fitzpatrick, Louis J ^a   Rivero, Ralph A ^a  

^a R W JOHNSON PHARMACEUTICAL RES I   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SULFONAMIDE; UREA DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; TECHNIQUE;

EID: 0030824831     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01795-4     Document Type: Article

References (21)

1. Merrifield R.B. J. Am. Chem. Soc. 85:1963;2149.
2. (a) Backes, B.J., Virgilio, A.A., Ellman, J.A. J. Am. Chem. Soc., 1996, 118, 3055.
3. (b) Backes, B.J., Ellman, J.A. J. Am. Chem. Soc. 1994, 116, 11171.
4. (c) Kenner, G.W. McDermott, J.R., Sheppard, R.C. J. Chem. Soc., Chem. Commun., 1971, 636.
5. Plunkett M.J., Ellman J.A. J. Org. Chem. 60:1995;6006.
6. Raju B., Kogan T.P. Tetrahedron Lett. 38:1997;3373.
7. (a) McManus, J.M.; Kuhla, D.E.; Wiederman, H.E.; Mayhew, D.E.; J. Med. Chem., 1976, 19, 1976.
8. (b) McManus, J.M.; McFarland, J.W.; Gerber, C.F.; McLamore, W.M.; Laubach, B.D. J. Med. Chem. 1965, 8, 766.
9. c) McFarland, J.W.; Gerber, C.F.; McLamore, W.M. J. Med. Chem., 1965, 8, 781.
10. (d) McManus, J.M.; Gerber, C.F. J. Med Chem, 1966, 9, 256.
11. (e) McManus, J.M. J. Med. Chem., 1966, 9, 967.
12. Picard J.A., O'Brien P.M., Sliskovic D.R., Anderson M.K., Bousley R.F., Hamelehle K.L., Krause B.R., Stanfield R.L. J. Med. Chem. 39:1996;1243.
13. Levitt, G. U.S. Patent 4, 786,311.
14. (a) Dhar, D.N.: Murthy, K.S.K.; Synthesis. 1986, 437.
15. (b) Rasmussen, J.K.; Hassner, A. Chem. Rev., 1976, 76, 389.
16. The use of scavenger resins to remove excess reagents is described in the following references: (a) Siegel, M.G.; Hahn, P.J.; Dressman, B.A.; Fritz, J.E.; Grunwell, JJ.R.; Kaldor, S.W. Tetrahedron Lett. 1997, 38, 3357.
17. (b) Kaldor, S.W.; Fritz, J. E.; Tang, J.; McKinney, E.R. Bioorg. Med. Chem. Lett. 1996, 6, 3041.
18. (c) Kaldor, S.W., Seigel, M.G.; Fritz, J.E.; Dressman, B.A.; Hahn, P.J. Tetrahedron Lett. 1996, 37, 7193.
19. (d) Booth, J.R.; Hodges, J.C. J. Am. Chem. Soc. 1997, 119, 4882.
20. +) 402 (M+H).
21. (2) amine during the washing steps.