Rapid catalyst identification for the synthesis of the pyrimidinone core of HIV integrase inhibitors

Angewandte Chemie - International Edition

Volumn 51, Issue 28, 2012, Pages 6912-6915

  Bellomo, Ana ^a   Celebi Olcum, Nihan ^b   Bu, Xiaodong ^c   Rivera, Nelo ^c   Ruck, Rebecca T ^c   Welch, Christopher J ^c   Houk, Kendall N ^b   Dreher, Spencer D ^c  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c MERCK RESEARCH LABORATORIES   (United States)

Author keywords

heterocycles; high throughput screening; homogeneous catalysis; P ligands; synthetic methods

Indexed keywords

HETEROCYCLES; HIGH-THROUGHPUT SCREENING; HOMOGENEOUS CATALYSIS; P LIGANDS; SYNTHETIC METHODS;

CHROMATOGRAPHY; EXPERIMENTS; REACTION KINETICS;

ELECTRON TRANSITIONS;

INTEGRASE; INTEGRASE INHIBITOR; PYRIMIDINONE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HIGH THROUGHPUT SCREENING; HUMAN; METABOLISM; METHODOLOGY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

CATALYSIS; HIGH-THROUGHPUT SCREENING ASSAYS; HIV INTEGRASE; HIV INTEGRASE INHIBITORS; HUMANS; MOLECULAR STRUCTURE; PYRIMIDINONES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84863694554     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201201720     Document Type: Article

References (25)

1. I. W. Davies, C. J. Welch, Science 2009, 325, 701.
2. S. D. Dreher, P. G. Dormer, D. L. Sandrock, G. A. Molander, J. Am. Chem. Soc. 2008, 130, 9257.
3. G. A. Molander, S. L. J. Trice, S. D. Dreher, J. Am. Chem. Soc. 2010, 132, 17701.
4. D. W. Robbins, J. F. Hartwig, Science 2011, 333, 1423.
5. A. McNally, C. K. Prier, D. W. C. MacMillan, Science 2011, 334, 1114.
6. M. T. Reetz, K. M. Kühling, A. Deege, H. Hinrichs, D. Belder, Angew. Chem. 2000, 112, 4049
7. Angew. Chem. Int. Ed. 2000, 39, 3891.
8. J. Kobayashi, Y. Mori, K. Okamoto, R. Akiyama, M. Ueno, T. Kitamori, S. Kobayashi, Science 2004, 304, 1305.
9. O. Trapp, S. K. Weber, S. Bauch, W. Hofstadt, Angew. Chem. 2007, 119, 7447
10. Angew. Chem. Int. Ed. 2007, 46, 7307.
11. G. R. Humphrey, P. J. Pye, Y.-L. Zhong, R. Angelaud, D. B. Askin, P. E. Maligres, D. E. Mancheno, R. A. Miller, R. A. Reamer, S. A. Weissman, Org. Process Res. Dev. 2011, 15, 73.
12. V. Summa, A. Petrocchi, F. Bonelli, B. Crescenzi, M. Donghi, M. Ferrara, F. Fiore, C. Gardelli, O. Gonzalez Paz, D. J. Hazuda, et al., J. Med. Chem. 2008, 51, 5843.
13. C. J. Welch, X. Gong, W. Schaefer, E. C. Pratt, T. Brkovic, Z. Prizada, J. F. Cuff, B. Kosjek, Tetrahedron: Asymmetry 2010, 21, 1674.
14. High-throughput Analysis in the Pharmaceutical Industry (Ed.:, P. G. Wang,), CRC Press, 2009.
15. D. E. O'Brien, L. T. Weinstock, R. H. Springer, C. C. Cheng, J. Heterocycl. Chem. 1967, 4, 49.
16. V. Summa, A. Petrocchi, V. G. Matassa, M. Taliani, R. Laufer, R. D. Francessco, S. Altmura, P. Pace, J. Med. Chem. 2004, 47, 5336.
17. E. Wagner, L. Becan, E. Nowakowska, Bioorg. Med. Chem. Lett. 2004, 12, 265.
18. S. D. Dreher, N. Ikemoto, V. Gresham, J. Liu, P. G. Dormer, J. Balsells, D. Mathre, T. J. Novak, J. D. I. Armstrong, Tetrahedron Lett. 2004, 45, 6023.
19. V. A. Boyd, J. Mason, P. Hanumesh, J. Price, C. J. Russell, T. R. Webb, J. Comb. Chem. 2009, 11, 1100.
20. Y.-L. Zhong, H. Zhou, D. R. Gauthier, J. Askin, Tetrahedron Lett. 2006, 47, 1315.
21. T. P. Culbertson, J. Heterocycl. Chem. 1979, 16, 1423.
22. P. J. Pye, Y.-L. Zhong, G. O. Jones, R. A. Reamer, K. N. Houk, D. Askin, Angew. Chem. 2008, 120, 4202
23. Angew. Chem. Int. Ed. 2008, 47, 4134.
24. Gaussian 09 (Revision A.02), M. J. Frisch, et al.; see the Supporting Information.
25. A. E. King, L. M. Huffman, A. Casitas, M. Costas, X. Ribas, S. S. Stahl, J. Am. Chem. Soc. 2010, 132, 12068, and references therein.