Development of HIV-integrase inhibitor S-1360: Selection of the protecting group on the 1,2,4-triazole ring

Organic Process Research and Development

Volumn 11, Issue 6, 2007, Pages 1055-1058

  Shimizu, Sumio ^a   Endo, Takeshi ^a   Izumi, Kenji ^a   Mikamiyama, Hidenori ^a  

^a SHIONOGI AND CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37048999747     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op700116y     Document Type: Article

References (18)

1. Nielsen, M. H.; Pedersen, F. S.; Kjems, J. Retrovirology 2005, 2, 10.
2. Greene, W. C. Nat. Immunol. 2004, 5, 867.
3. (a) De Clercq, E. Med. Res. Rev. 2002, 22, 531.
4. (b) De Clercq, E. Expert Opin. Emerg. Drugs 2005, 10, 241.
5. Fujishita, T.; Yoshinaga, T.; Sato, A. PCT Int Appl. WO 2000039086A, 2000.
6. (a) Uenaka, M.; Kawata, K.; Nagai, M.; Endo, T. PCT Int. Appl. WO 2000075122, 2000.
7. (b) Shimizu, S.; Nishino, Y.; Yoshida, K. PCT Int. Appl. WO 2003042189, 2003.
8. Izumi, K.; Kabaki, M.; Uenaka, M.; Shimizu, S. Org. Process Res. Dev. 2007, 11, 1059.
9. Vemishetti, P.; Leiby, R. W.; Abushanab, E.; Panzica, R. P. J. Heterocycl. Chem. 1988, 25, 651. This material was purchased from Masuda Chemical Industries Co. Ltd., Tateyama Kasei Co. Ltd. and Otsuka Chemical Co. Ltd.
10. 3): δ 1.01 (3H, t, J = 7.2 Hz), 3.76(2H, q, J = 7.2 Hz), 7.10-7.17 (6H, m), 7.28-7.36 (9H, m), 8.00 (1H, s).
11. The structure of 5a was determined by the X-ray structural analysis. The detail data are included in Supporting Information.
12. Atsumi, T.; Kai, Y.; Katsube, J. Jpn. Kokai Tokkyo Koho JP-52068182, 1977.
13. Dallacker, F.; Minn, K. Chem. Ztg. 1986, 110, 275.
14. 1H NMR spectra of similar triazole compounds, see: Vemishetti, P.; Leiby, R. W.; Abushanab, E.; Panzica, R. P. J. Heterocyl. Chem. 1988, 25, 651.
15. (b) Ramasamy, K. S.; Tam, R. C.; Bard, J.; Averett, D. R. J. Med. Chem. 2000, 43, 1019.
16. (c) Kim, M. J.; Chung, S. Y.; Chun, M. W. Synth. Commun. 2005, 35, 2653.
17. Similarly, selective alkylation of methyl 1H-1,2,4-triazole-3- carboxylate has been reported; see: Zhang, P.; Dong, Z. E.; Cleary, T. P. Org. Process Res. Dev. 2005, 9, 583.
18. The protecting group position of 6b is confirmed by the HMBC correlation for the pyranyl methine proton to the triazole C-5 and without the HMBC correlation for the pyranyl methine proton to the triazole C-3. The detail data are included in Supporting Information.