A practical synthesis of m-prostaglandin E synthase-1 inhibitor MK-7285

Journal of Organic Chemistry

Volumn 74, Issue 20, 2009, Pages 7790-7797

  Gosselin, Francis ^a   Lau, Stephen ^a   Nadeau, Christian ^a   Trinh, Thao ^a   O'Shea, Paul D ^a   Davies, Ian W ^b  

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANIONIC CYCLIZATION; CHEMICAL EQUATIONS; CHROMATOGRAPHY-FREE SYNTHESIS; CYANATION; DIRECTED ORTHO-METALATION; PROSTAGLANDINE; SYNTHASES;

AMIDES; CHEMICAL REACTIONS; CHROMATOGRAPHIC ANALYSIS;

ENZYMES;

1 [ 9 ( 2 CYCLOPROPYLETHOXY) 2 ( 2,6 DIBROMO 4 FLUOROPHENYL) 1H PHENANTHRO[ 9,10 D]IMIDAZOL 9 YL] 2 METHYLPROPAN 2 OL; 2 [ 9 ( 2 CYCLOPROPYLETHOXY) 6 ( 2 HYDROXY 2 METHYLPROPYL) 1H PHENANTHRO[ 9,10 D]IMIDAZO 2 YL] 5 FLUOROISOPHTHALONITRILE; 3 ( 2 CYCLOPROPYLETHOXY) 6 ( 2 HYDROXY 2 METHYLPROPYL)PHENANTHREN 9,10 DIONE; 5 ( 2 CYCLOPROPYLETHOXY) 5' ( 2 HYDROXY 2 METHYLPROPYL) 2' METHYLBIPHENYL 2 CARBOXYLIC ACID DIETHYL AMIDE; 6 ( 2 CYCLOPROPYLETHOXY) 3,3 ( 2 HYDROXY 2 METHYLPROPYL)PHENANTHREN 9 OL; CARBOXYLIC ACID DERIVATIVE; IMIDAZOLE; IMIDAZOLE DERIVATIVE; MK 7285; PHENANTHRENE DERIVATIVE; PROSTAGLANDIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CHROMATOGRAPHY; CROSS COUPLING REACTION; CYANATION; CYCLIZATION; DIAZOTIZATION; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; METALLATION; SUBSTITUTION REACTION;

CYCLIZATION; ENZYME INHIBITORS; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; INTRAMOLECULAR OXIDOREDUCTASES; MOLECULAR STRUCTURE;

EID: 70349854525     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901798d     Document Type: Article

References (50)

1. Funk, C. D. Science 2001, 294, 1871.
2. (a) Jakobsson, P. J.; Thoren, S.; Morgenstern, R.; Samuelsson, B. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 7220.
3. (b) Murakami, M.; Naraba, H.; Tanioka, T.; Semmyo, N.; Nakatani, Y.; Kojima, F.; Ikeda, T.; Fueki, M.; Ueno, A.; Oh, S.; Kudo, I. J. Biol. Chem. 2000, 275, 32783.
4. (c) Murakami, M.; Kudo, I. Prog. Lipid Res. 2004, 43, 3.
5. Kojima,F.;Kato, S.;Kawai, S. Fund. Clin.Pharmacol. 2005, 19, 255-261.
6. (a) Giroux, A.; Boulet, L.; Brideau, C.; Chau, A.; Claveau, D.; Côté, B.; Ethier, D.; Frenette, R.; Gagnon, M.; Guay, J.; Guiral, S.; Mancini, J.; Martins, E.; Massé, F.; Méthot, N.; Riendeau, D.; Rubin, J.; Xu, D.; Yu, H.; Ducharme, Y.; Friesen, R. W. Bioorg. Med. Chem. Lett. 2009, in press.
7. (b) Côté, B.; Boulet, L.; Brideau, C.; Claveau, D.; Ethier, D.; Frenette, R.; Gagnon, M.; Giroux, A.; Guay, J.; Guiral, S.; Mancini, J.; Martins, E.; Massé, F.; Méthot, N.; Riendeau, D.; Rubin, J.; Xu, D.; Yu, H.; Ducharme, Y.; Friesen, R. W. Bioorg. Med. Chem. Lett. 2007, 17, 6816.
8. (a) de Silva, S. O.; Reed, J. N.; Snieckus, V. Tetrahedron Lett. 1978, 19, 5099.
9. (b) Cheng, W.; Snieckus, V. Tetrahedron Lett. 1987, 28, 5097.
10. (c) Reviewed in: Anctil, E. J.-G.; Snieckus, V. Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; Wiley-VCH: New York, 2004; Vol.2, pp 761-813.
11. (a) Wang, X.; Snieckus,V. Tetrahedron Lett. 1991, 32, 4879.
12. (b) Wang, X.; Snieckus, V. Tetrahedron Lett. 1991, 32, 4883.
13. (c) Cai, X.; Brown, S.; Hodson, P.; Snieckus, V. Can. J. Chem. 2004, 82, 195.
14. (d) A related approach has been reported recently: Limanto, J.; Dorner, B. T.; Hartner, F. W.; Tan, L. Org. Proc. Res. Dev. 2008, 12, 1269.
15. Doyle, M. P.; Bryker, W. J. J. Org. Chem. 1979, 44, 1572.
16. Molinaro, C.; Mowat, J.; Gosselin, F.; O'Shea, P. D.; Marcoux, J.-F.; Angelaud, R.; Davies, I. W. J. Org. Chem. 2007, 72, 1856.
17. Diazonium tetrafluoroborate salt 6 was deemed bench-stable as it exhibited an exotherm of 35.8 cal/g initiating at 100°C and a smaller exotherm of 3.5 cal/g initiating at 175°C asmeasured by differential scanning calorimetry.
18. (a) Maruoka, K.; Fukutani, Y.; Yamamoto, H. J. Org. Chem. 1985, 50, 4412.
19. (b) Russo, J. M.; Price, W. A. J. Org. Chem. 1993, 58, 3589.
20. (c) For a review, see: Charette, A. B.; Beauchemin, A. Org. React. 2001, 58, 1.
21. (a) Kim, A.; Powers, J. D.; Toczko, J. F. J. Org. Chem. 2006, 71, 2170.
22. (b) Rodriguez, J. R.; Agejas, J.; Bueno, A. B. Tetrahedron Lett. 2006, 47, 5661.
23. (c) Woiwode, T. F.; Rose, C.; Wandless, T. J. J. Org. Chem. 1998, 63, 9594.
24. (a) Campeau, L.-C.; Stuart, D. R.; Leclerc, J.-P.; Bertrand-Laperle, M.; Villemure, E.; Sun, H.-Y; Lasserre, S.; Guimond, N.; Lecavallier, M.; Fagnou, K. J. Am. Chem. Soc. 2009, 131, 3291.
25. (b) Campeau, L.-C.; Parisien, M.; Jean, A.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 581.
26. (c) Lafrance, M.; Rowley, C. N.; Woo, T. K.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 8754.
27. (d) Lafrance, M.; Shore, D.; Fagnou, K. Org. Lett. 2006, 8, 5097.
28. (a) Streitweiser, A; Mares, F. J. Am. Chem. Soc. 1968, 90, 644.
29. (b) Streitweiser, A.; Scannon, P. J.; Niemeyer, H. M. J. Am. Chem. Soc. 1975, 97, 7936.
30. (c) Bridges, A. J.; Lee, A.; Maduakor, E. C.; Schwartz, C. E. Tetrahedron Lett. 1992, 33, 7495.
31. (a) Winkle, M. R.; Ronald, R. C. J. Org. Chem. 1982, 47, 2101.
32. (b) Fraser, R. R.; Bresse, M.; Mansour, T. S. J. Am. Chem. Soc. 1983, 105, 7790.
33. (a) Nagano, T. J. Org. Chem. 1957, 22, 817.
34. (b) Cushman, M.; Patel, H. H.; Scheuring, J.; Bacher, A. J. Org. Chem. 1992, 57, 5630.
35. 6 showed multiple signals in the aromatic region as well as large singlet at 1.45 ppm which account for the t-Bu group.
36. (a) Alam, A. Synlett 2005, 2403.
37. (b) Chassaing, C.; Haudrechy, A.; Langlois, Y. Tetrahedron Lett. 1997, 38, 4415.
38. (a) For a review, see: Ellis, G. P.; Romney-Alexander, T. Chem. Rev. 1987, 87, 779-794.
39. (b) Merz, V.; Weith, W. Ber. 1877, 10, 746.
40. For a review, see: (a) Sundermeier, M.; Zapf, A.; Beller, M. Eur. J. Inorg. Chem. 2003, 3513. For several examples, see:
41. (b) Anderson, B. A.; Bell, E. C.; Ginah, F. O.; Harn, N. K.; Pagh, L. M.; Wepsiec, J. P. J. Org. Chem. 1998, 63, 8224.
42. (c) Tschaen, D. M.; Desmond, R.; King, A. O.; Fortin, M. C.; Pipik, B.; King, S.; Verhoeven, T. R. Synth. Commun. 1994, 24, 887.
43. (d) Weissman, S. A.; Zewge, D.; Chen, C. J. Org. Chem. 2005, 70, 1508.
44. (a) Schareina, T.; Zapf, A.; Mägerlein, W.; Müller, N.; Beller, M. Synlett 2007, 555.
45. (b) Schareina, T.; Zapf, A.; Mägerlein, W.; Müller, N.; Beller, M. Chem. - Eur. J. 2007, 13, 6249.
46. We presume that the formation of the chloroaldehyde analogue occurs during the halogen-metal exchange reaction via benzyne formation. Careful GC-MS analysis of starting material 22 did not show any chloro-22. (a) Villieras, J. Bull. Soc. Chim. Fr. 1967, 5, 1520.
47. (b) Villieras, J.; Kirschleger, B.; Tarhouni, R.; Rambaud, M. Bull. Soc. Chim. Fr. 1986, 470.
48. (c) Reviewed in: Knochel, P.; Dohle, W.; Gommermann, N.; Kneisel, F. F.; Kopp, F.; Korn, T.; Sapountzis, I.; Vu, V. A. Angew. Chem., Int. Ed. 2003, 42, 4302-4320.
49. (d) Wang, X.-J.; Sun, X.; Zhang, L.; Xu, Y.; Krishnamurthy, D.; Senanayake, C. H. Org. Lett. 2006, 8, 305-307.
50. Aycock, D. F. Org. Proc. Res. Dev. 2007, 11, 156.