Process development of a potent bradykinin 1 antagonist

Organic Process Research and Development

Volumn 13, Issue 3, 2009, Pages 519-524

  Menzel, Karsten ^a   Machrouhi, Fouzia ^a   Bodenstein, Matthew ^a   Alorati, Anthony ^a   Cowden, Cameron ^a   Gibson, Andrew W ^a   Bishop, Brian ^a   Ikemoto, Norihiro ^a   Nelson, Todd D ^a   Kress, Michael H ^a   Frantz, Doug E ^b  

^a MERCK RESEARCH LABORATORIES   (United States)

^b UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 66249130619     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op8003184     Document Type: Article

References (23)

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11. As determined by HPLC versus a standard isolated, purified, and characterized by 1H- and 13C NMR.
12. Interestingly, in contrast to Burton's observation, in which a rearrangement reaction of a lithiated anion in the 3-position of 1,2,4- trichlorobenzene occured after trapping and aging the reaction mixture in the presence of DMF, a similar observation with the Grignard reagent was not observed. Burton, A. J.; Cardwell, K. S.; Fuchter, M. J.; Lindvall, M. K.; Patel, R.; Packham, T. W.; Prodger, J. C.; Schilling, M. B.; Walker, M. D. Tetrahedron Lett. 2003, 5653.
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14. Succinimide side product of 10 was proposed by mass spectrometric analysis and is believed to be 1-((2-bromo-4-chloro-6-fluoro-phenyl)- [(E)-hydroxyimino]methyl)pyrrolidine-2,5-dione.
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17. LCAP: HPLC area percent; LCWP: HPLC weight percent.
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22. The acid C was commercially available on kilogram scale from Lonza. Shaw, N. M.; Naughton, A.; Robins, K.; Tinschert, A.; Schmid, E.; Hischier, M.-L.; Venetz, V.; Werlen, J.; Zimmermann, T.; Brieden, W.; Riedmatten, P.; de Roduit, J.-P.; Zimmermann, B.; Neumuller, R. Org. Process Res. Dev. 2002, 6, 497.
23. loro-3,4-dibromo-5-fluorobenzene is commercially available from Acros.