Novel approaches towards the LTD4/E4 antagonist, LY290154

Organic Process Research and Development

Volumn 10, Issue 4, 2006, Pages 776-783

  Merschaert, Alain ^a   Boquel, Pascal ^a   Van Hoeck, Jean Pierre ^a   Gorissen, Hugo ^a   Borghese, Alfio ^a   Bonnier, Benjamin ^a   Mockel, Anne ^a   Napora, Freddy ^a  

^a Eli Lilly Benelux   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33746892307     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op060036x     Document Type: Article

References (30)

1. Gilmore, J.; Todd, A. Eur. Pat. Appl. EP469833, 1992.
2. Brennan, J.; Dobson, D.; Gilmore, J.; Gorissen, H. J.; Huff, B.; Journee, G.; Kennedy, J. H.; Sawyer, J. S.; Todd, A.; Weigel, L. O. Lilly Research Laboratories. Presented at 209th ACS National Meeting, April 2, 1995, Anaheim, CA; American Chemical Society: Washington, DC, 1995.
3. (a) Young, R. N.; Senneville, R.; Longueil, Z.; Leger, S.; Ormeaux, D. U. S. Patent 4,851,409, 1989.
4. (b) McNamara, J. M.; Leazer, J. L.; Bhupathy, M.; Amota, J. S.; Reamer, R. A.; Reider, P. J.; Grabowski, E. J. J. J. Org. Chem. 1989, 54, 3718.
5. (a) Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem. 1988, 53, 2390.
6. (b) Knochel, P.; Xiao, C.; Yeh, M. C. P. Tetrahedron Lett. 1988, 29, 6697.
7. (c) Presently commercially available from Aldrich.
8. Bose, A. K.; Lal, B. Tetrahedron. Lett. 1973, 14, 3937.
9. Cyanomethoxyindole can be purchased from Biosynth A.G. For a preparative method, see: Dobson, D.; Todd, A.; Gilomore, J. Synth. Commun. 1991, 21, 611.
10. Typically required SG filtration + 2 Waters PHPLC-2000 chromatographic purifications.
11. Huff, B. E.; Staszak, M. A. Tetrahedron Lett, 1993, 34, 8011.
12. Kumar, Y.; Florvall, L. Synth. Commun. 1973, 13, 489.
13. Ballistreri, F. P.; Maccarone, E.; Musumarra, G.; Tomaselli, G. A. J. Org. Chem. 1977, 42, 1415.
14. (a) Swain, C. G. J. Am. Chem. Soc. 1948, 70, 1119.
15. (b) Swain, C. G.; Eddy, R. W. J. Am. Chem. Soc. 1948, 70, 2989.
16. (c) Swain, C. G.; Langsdorf, W. P. J. Am. Chem. Soc. 1951, 73, 2813.
17. (d) Swain, C. G.; Scott, C. B. J. Am. Chem. Soc. 1953, 75, 141.
18. (e) Swain, C. G.; Mosely, R. B.; Bown, D. E. J. Am. Chem. Soc. 1955, 77, 3731.
19. Walker, D.; Hiebert, J. D. Chem. Rev. 1967, 67, 153.
20. Bach, N. J.; Baker, S. R.; Gilmore, J.; Lewthwaite, R. A.; McKillop, A.; Sawyer, J. S.; Stephenson, G. R.; Urquhart, M. W. J. Eur. Pat Appl. EP 0775694 A2, 1997; Chem. Abstr. 127: 81355.
21. For a preparation of 7-chloro-2-vinyl-quinoline, see: Larsen, R. D.; Corley, E. G.; King, A. O.; Caroll, J. D.; Davis, P.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1996, 61, 3398.
22. (a) Katritzky, A. R.; Lan, X.; Fan, W. Q. Synthesis 1994, 445.
23. (b) Katritzky, A. R.; Rachwal, S.; Hitchings, G. J. Tetrahedron 1991, 47, 2683 and references therein.
24. Yamauchi, M. Chem. Pharm. Bull. 1993, 41, 2042.
25. A 12-step asymmetric synthesis (2.4% overall yield) was also developed. See ref 13 and Montalban, A. G. Ph.D. Thesis, University of East Anglia, Norwich, 1995. The key results of this work were presented by Prof. McKillop at the ChiRex Technical Symposium, Newcastle, June 27, 1996.
26. Mancuso, A. J.; Swern, D. Synthesis 1981, 165.
27. (a) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551.
28. (b) Corey, E. J.; Bakshi, R. K.; Shibata, S.; Chen, C. P.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925.
29. Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521.
30. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.