Regioselective synthesis of benzimidazole thiophene inhibitors of polo-like kinase 1

Tetrahedron Letters

Volumn 49, Issue 44, 2008, Pages 6348-6351

  Hornberger, Keith R ^a   Badiang, Jennifer G ^a   Salovich, James M ^a   Kuntz, Kevin W ^a   Emmitte, Kyle A ^a   Cheung, Mui ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

Amination; Benzimidazoles; Catalysis; Palladium catalyzed; PLK

Indexed keywords

1 (2 THIENYL)BENZIMIDAZOLE; BENZIMIDAZOLE DERIVATIVE; BROMOBENZENE; GSK 461364; NITROBENZENE DERIVATIVE; PALLADIUM; POLO LIKE KINASE 1; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYSIS; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; REDUCTION KINETICS; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

EID: 51549109898     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.08.077     Document Type: Article

References (26)

1. Barr F.A., Silljé H.H.W., and Nigg E.A. Nat. Rev. Mol. Cell Biol. 5 (2004) 429-440
2. Strebhardt K., and Ullrich A. Nat. Rev. Cancer 6 (2006) 321-330
3. Goh K.C., Wang H., Yu N., Zhou Y., Zheng Y., Lim Z., Sangthongpitag K., Fang L., Du M., Wang X., Jefferson A.B., Rose J., Shamoon B., Reinhard C., Carte B., Entzeroth M., Ni B., Taylor M.L., and Stünkel W. Drug Dev. Res. 62 (2004) 349-361
4. McInnes C., Mezna M., and Fischer P.M. Curr. Top. Med. Chem. 5 (2005) 181-197
5. Hofheinz R., Hochhaus A., Al-Batran S., Nanci A., Reichardt V., Trommeshauser D., Hoffmann M., Steegmaier M., Munzert G., and Jäger E. J. Clin. Oncol. 24 (2006) 2038
6. Munzert G., Steinbild S., Frost A., Hedborn S., Rentschler J., Kaiser R., Trommeshauser D., Hoffmann M., Steegmaier M., and Mross K. J. Clin. Oncol. 24 (2006) 3069
7. Lansing T.J., McConnell R.T., Duckett D.R., Spehar G.M., Knick V.B., Hassler D.F., Noro N., Furuta M., Emmitte K.A., Gilmer T.M., Mook Jr. R.A., and Cheung M. Mol. Cancer Ther. 6 (2007) 450-459
8. Andrews, C. W., III; Cheung, M.; Davis-Ward, R. G.; Drewry, D. H.; Emmitte, K. A.; Hubbard, R. D.; Kuntz, K. W.; Linn, J. A.; Mook, R. A.; Smith, G. K.; Veal, J. M. Preparation of benzimidazolyl substituted thiophenes as Polo like kinases (PLK) inhibitors for treating cancer. PCT Int. Appl. WO2004014899.
9. Kuntz, K. W.; Salovich, J. M.; Mook, R.A., Jr.; Emmitte, K. A.; Chamberlain, S. D.; Rheault, T. R.; Hornberger, K. R.; Emerson, H. K.; Smith, S. C.; Wilson, B. J.; Davis-Ward, R. G.; Donaldson, K. H.; Adjabeng, G. M.; Nailor, K. E.; Hassler, D. F.; Smith, G. K.; Lansing, T. J.; Duckett, D.; Knick, V.; McConnell, R. T.; Jackson, J. R.; Cheung, M. Identification of GSK461364, a novel small molecule polo-like kinase 1 inhibitor for the treatment of cancer. 2007 AACR Annual Meeting, Los Angeles, CA, April 2007, Abstract 4171.
10. Corral C., and Lissavetzky J. Synthesis (1984) 847-850
11. Emmitte, K. A.; Cheung, M. Process for Preparing Benzimidazole Thiophenes. PCT Int. Appl. WO2005037827.
12. Grimmett M.R. Science of Synthesis. In: Neier R. (Ed). Product Class 4: Benzimidazoles (2002), Springer, New York 529-612
13. Preston P.N. Chem. Rev. 74 (1974) 279-314
14. Hornberger K.R., Adjabeng G.M., Dickson H.D., and Davis-Ward R.G. Tetrahedron Lett. 47 (2006) 5359-5361 and references therein
15. See Supplementary material for the synthesis of 6.
16. Zim D., and Buchwald S.L. Org. Lett. 5 (2003) 2413-2415
17. Huang X., Anderson K.W., Zim D., Jiang L., Klapars A., and Buchwald S.L. J. Am. Chem. Soc. 125 (2003) 6653-6655
18. Gujadhur R., Venkataraman D., and Kintigh J.T. Tetrahedron Lett. 42 (2001) 4791-4793
19. Wolfe J.P., Tomori H., Sadighi J.P., Yin J., and Buchwald S.L. J. Org. Chem. 65 (2000) 1158-1174
20. Hamann B.C., and Hartwig J.F. J. Am. Chem. Soc. 120 (1998) 7369-7370
21. Driver M.S., and Hartwig J.F. J. Am. Chem. Soc. 118 (1996) 7217-7218
22. Yin J., Zhao M.M., Huffman M.A., and McNamara J.M. Org. Lett. 4 (2002) 3481-3484
23. + 603.1413, found 603.1409.
24. For alternative Pd-catalyzed amination approaches to benzimidazoles, see:. Brain C.T., and Brunton S.A. Tetrahedron Lett. 43 (2002) 1893-1895
25. Rivas F.M., Giessert A.J., and Diver S.T. J. Org. Chem. 67 (2002) 1708-1711
26. Zheng N., Anderson K.W., Huang X., Nguyen H.N., and Buchwald S.L. Angew. Chem., Int. Ed. 46 (2007) 7509-7512