A facile and scaleable synthesis of ABT-239, a benzofuranoid H3 antagonist

Organic Process Research and Development

Volumn 9, Issue 1, 2005, Pages 45-50

  Pu, Yu Ming ^a   Grieme, Timothy ^a   Gupta, Ashok ^a   Plata, Daniel ^a   Bhatia, Ashok V ^a   Cowart, Marlon ^a,b   Ku, Yi Yin ^a  

^a ABBOTT LABORATORIES   (United States)

^b Neuroscience Research

Author keywords

[No Author keywords available]

Indexed keywords

5 (4 CYANOPHENYL) 2 [2 (2 METHYL 1 IMIDAZOLIDINYL)ETHYL]BENZOFURAN; CYANIDE; FURAN DERIVATIVE; HISTAMINE 3 RECEPTOR BLOCKING AGENT; PALLADIUM; PHENOL; RECEPTOR BLOCKING AGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CROSS COUPLING REACTION; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; PHASE SEPARATION; QUANTITATIVE ANALYSIS; REACTION ANALYSIS;

EID: 13844297634     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op049809c     Document Type: Article

References (16)

1. Leurs, R.; Blandina, P.; Tedford, C.; Timmerman, H. Trends Pharmacol. Sci. 1998, 19, 177.
2. Stark, H. Curr. Opin. Ther. Pat. 2003, 13, 851.
3. (a) Aslanian, R.; Mutahi, M. W.; Shih, N.-Y.; McCormick, K. D.; Piwinski, J. J.; Ting, P. C.; Albanese, M. M.; Berlin, M. Y.; Zhu, X.; Wong, S.-C.; Rosenblum, S. B.; Jiang, Y.; West, R.; She, S.; Williams, S. M.; Bryant, M.; Hey, J. A. Bioorg. Med. Chem. Lett. 2002, 12, 937.
4. (b) Huers. A.; Purand, K.; Stark, H.; Ligneau, X.; Arrang, J.-M.; Schwarts, J.-C.; Schunack, W. Bioorg. Med. Chem. Lett. 1996, 6, 2013.
5. Cowart, M.; Pratt, J. K.; Stewart, A. O.; Bennani, Y. L.; Esbenshade, T. A.; Hancock, A. A. Bioorg. Med. Chem. Lett. 2004, 14, 689.
6. Kumar, V.; Ackerman, J. H.; Alexander, M. D.; Bell, M. R.; Christiansen, R. G.; Duan, J. S.; Jaeger, E. P., Herrmann, J. L., Jr.; Krolski, M. E.; McKloskey, P.; Batzold, F. H.; Juniewicz, P. E.; Rell, J.; Snyder, B. W.; Winneker, R. C. J. Med. Chem. 1994, 37, 4227.
7. Ohemeng, K. A.; Appollina, M. A.; Nguyen, V. N.; Schwender, C. F.; Singer, M.; Steber, M.; Ansell, J.; Argentieri, D.; Hageman, W. J. Med. Chem. 1994, 37, 3663.
8. Trost, B. M., Fleming, I., Eds. Comprehensive Organic Synthesis: Selectivity, Strategy, and Efficiency in Modern Organic Chemistry; Pergamon Press: New York, 1991; Vol 2, pp 368-376.
9. Monteiro, N.; Balme, G. Synlett 1998, 746.
10. Nijhuis, W. H. N.; Verboom, W.; El-Fadl, A. A.; Hummel, G. J. V.; Reinhoudt, D. N. J. Org. Chem. 1989, 54, 209.
11. Castanet, A.-S.; Colobert, F.; Broutin, P.-E. Tetrahedron Lett. 2002, 43, 5047.
12. Kelly, S. M. Helv. Chim. Acta 1989, 72, 594.
13. Andres, J. M.; Herraiz-Sierra, I.; Pedrosa, R.; Perez-Encabo, A. Eur. J. Org. Chem. 2000, 1719.
14. (a) Karrer, P.; Ehrhart, K. Helv. Chim. Acta 1951, 34, 2202.
15. (b) Kuil, L. A.; Veldhuizen, Y. S. J.; Grove, D. M.; Zwikker, L. J. W.; Jenneskens, L. W.; Drenth, W.; Smeets, W. J. J.; Spek, A. L.; Koten, G. Recl. Trav. Chim. Pays-Bas 1994, 113, 267.
16. Cbz valine anhydride is a crystalline solid, and it can be readily prepared in high chemical and enantiomeric purity from Cbz-valine with DDC. See: Leanna, M. R.; Hannick, S. M.; Rasmussen, M.; Tien, J.-h. J.; Bhagavatula, L.; Singam, P. R.; Gates, B. D.; Kolaczkowski, L.; Patel, R. R.; Wayne, G.; Lannoye, G.; Zhang, W.; Lukin, K. A.; Narayanan, B.; Riley, D. A.; Morton, H.; Chang, S.-J.; Curty, C. B.; Plata, D.; Bellettini, J.; Shellat, B.; Spitz, T.; Yang, C.-X. PCT Int. Appl. WO 2000008025 A1 20000217, 2000, 92 pp.