A new method for synthesis of nolatrexed dihydrochloride

Organic Process Research and Development

Volumn 14, Issue 2, 2010, Pages 346-350

  Xue, Xiaowen ^a,c   Zhao, Xueqing ^a   Li, Fei ^b   Zhuang, Weiping ^a   Lian, Yuanyang ^a   Fan, Jianhui ^a   Fang, Dongsheng ^a  

^a FUJIAN INSTITUTE OF MICROBIOLOGY   (China)

^b NANJING MEDICAL UNIVERSITY   (China)

^c CHINA PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77950184283     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op9002517     Document Type: Article

References (27)

1. Niculescu-Duvaz, L. Curr. Opin. Invest. Drugs 2001, 2 (5), 693-705.
2. Chu, E.; Callender, M. A.; Farrell, M. P.; Schmitz, J. C. Cancer Chemother. Pharmacol. 2003, 52 (suppl. 1), S80-89.
3. Rustum, Y. M.; Harstrick, A.; Cao, S.; Vanhoefer, U.; Yin, M. B.; Wilke, H.; Seeber, S. J. Clin. Oncol. 1997, 15, 389-400.
4. Schiffer, C. A.; Clifton, I. J.; Davisson, V. J.; Santi, D. V.; Stroud, R. M. Biochemistry 1995, 34, 16279-16287.
5. Staurt, K.; Tessitore, J.; Rudy, J.; Clendennin, N.; Johnston, A. Cancer 1999, 86, 410-414.
6. Mok, T. S. K.; Leung, T. W. T.; Lee, S.-D.; Chao, Y.; Chan, A. T. C.; Huang, A.; Lui, M.-C.; Yeo, W.; Chak, K.; Johnston, A.; Johnson, P. Cancer Chemother. Pharmacol. 1999, 44, 307-311.
7. Gish, R. G.; Wadler, S. J. Clin. Oncol. 2004, 22 (14S), 4260. ASCO Annual Meeting Proceedings (Post-Meeting Edition), July 15, Supplement.
8. (a) Webber, S. E.; Bleckman, T. M.; Attard, J.; Deal, J. G.; Kathardekar, V.; Welsh, K. M.; Webber, S.; Janson, C. A.; Matthews, D. A.; Smith, W. W.; Freer, S. T.; Jordan, S. R.; Bacquet, R. J.; Howland, E. F.; Booth, C. L. J.; Ward, R. W.; Hermann, S. M.; White, J.; Morse, C. A.; Hilliard, J. A.; Bartlett, C. A. J. Med. Chem. 1993, 36, 733-746.
9. (b) Webber, S. E.; Bleckman, T. M.; Attard, J.; Jones, T. R.; Varney, M. D. Antiproliferative Quinazolines. U.S. Patent 5,707,992, 1998.
10. Chen, W.-M.; Wan, S.-H. Synth. Commun. 2007, 37, 53-61.
11. Malmgren, H.; Bäckström, B.; Sølver, E.; Wennerberg, J. Org. Process Res. Dev. 2008, 12, 1195-1200.
12. Zeghida, W.; Debray, J.; Chierici, S.; Dumy, P.; Demeunynck, M. J. Org. Chem. 2008, 73 (6), 2473-2475.
13. Lecher, H. Z.; Kosloski, C. L. Halo-formamidine Salts and Method of Preparation. U.S. Patent 2,727,922, 1955.
14. (a) Reissenweber, G.; Mangold, D. Preparation of alkyl anthranilate. U.S. Patent 4,310,677, 1982.
15. (b) Reissenweber, G.; Mangold, D. Angew. Chem., Int. Ed. Engl. 1981, 20 (10), 882-883.
16. 14. By following the reference,12 chloroformamidine hydrochloride (9) was prepared in 84% yield; White crystals; Mp 134-138 °C dec; IR (KBr, cm-1): 3463, 3033, 2248, 1692, 1612, 1413; CH4N2Cl2 (114.963) calculated: C 10.45, H 3.51, N 24.37; found C 10.27, H 3.59, N 24.65.
17. (a) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 238, 2237-2264.
18. (b) Kim, J.-H.; Bang, S. W. Polym. J. 2000, 32 (2), 2000.
19. (c) Kametani, T.; Fukumoto, K. J. Chem. Soc. 1964, 6141-6146.
20. (d) Kuratsu, M.; Kozaki, M.; Okada, K. Chem. Lett. 2004, 33 (9), 1174-1175.
21. (e) McMorran, D. A.; Steel, P. J. Acta Crystallogr. 1998, C54, 1132-1133.
22. (f) Jahng, Y.; Telford, J. R. Bull. Korean Chem. Soc. 2005, 26 (10), 1614-1615.
23. (g) Sperotto, E.; Van Klink, G. P. M.; De Vries, J. G.; Van Koten, G. J. Org. Chem. 2008, 73, 5625-5628.
24. (h) Klapars, A.; Buchwald, S. L. Org. Lett. 2001, 3, 3803-3805.
25. (i) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581-584.
26. For details about the formation of 4,4′-dithiodipyridine, see: Yamamoto, T.; Sekine, Y. Can. J. Chem. 1984, 62, 1544-1547.
27. Spectrum ID: WHSP48928 in Integration Spectral Database System of Organic Compounds. Data were obtained from the National Institute of Advanced Industrial Science and Technology.