Development of a scalable process for 1-(3,5-dichlorophenyl)-5-iodo-3- methyl-(4-methylbenzyl)-1H-imidazo[1,2-a]imidazol-2-one: A key intermediate for the synthesis of LFA-1 inhibitors

Organic Process Research and Development

Volumn 9, Issue 2, 2005, Pages 137-140

  Frutos, Rogelio P ^a   Eriksson, Magnus ^a   Wang, Xiao Jun ^a   Byrne, Denis ^a   Varsolona, Richard ^a   Johnson, Michael D ^a   Nummy, Lawrence ^a   Krishnamurthy, Dhileepkumar ^a   Senanayake, Chris H ^a  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (3,5 DICHLOROPHENYL) 5 IODO 3 METHYL(4 METHYLBENZYL) 1H IMIDAZO[1,2 A]IMIDAZOL 2 ONE; IMIDAZOLE DERIVATIVE; IMMUNOLOGIC AGENT; IODINE DERIVATIVE; LYMPHOCYTE FUNCTION ASSOCIATED ANTIGEN 1; UNCLASSIFIED DRUG; VINYL IODIDE;

ARTICLE; CHEMICAL PROCEDURES; CHROMATOGRAPHY; DRUG SYNTHESIS; PILOT STUDY; REPRODUCIBILITY;

EID: 17444364170     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op049813o     Document Type: Article

References (8)

1. Springer, T. A. Nature 1990, 346, 425.
2. Wu, J.-P.; Emeigh, J.; Gao, D. A.; Goldberg, D. R.; Kuzmich, D.; Miao, C.; Potocki, I.; Qian, K. C.; Sorcek, R. J.; Jeanfavre, D. D.; Kishimoto, K.; Mainolfi, E. A.; Nabozni, G.; Peng, C.; Reilly, P.; Rothlein, R.; Sellati, R. H.; Woska, J. R.; Chen, S.; Gunn, J. A.; O'Brien, D.; Norris, S. H.; Kelly, T. A. J. Med. Chem. 2004, 5356 and references therein.
3. (a) Yee, N. K. Org. Lett. 2000, 2, 2781.
4. (b) Frutos, R. P.; Stehle, S.; Nummy, L.; Yee, N. Tetrahedron: Asymmetry 2001, 12, 101.
5. Frutos, R. P.; Johnson, M. Tetrahedron Lett. 2003, 44, 6509.
6. Lee, K.; Wiemer, D. F. Tetrahedron Lett. 1993, 34, 2433.
7. Alternative procedures for the multi-kilogram production of 6 have been developed. For additional information on the subject, see Wang, X.-j.; Zhang, L.; Xu, Y.; Krishamurthy, D.; Varsolona, R.; Nummy, L.; Frutos, R. P.; Byrne, D.; Chung, J. C.; Farina, V.; Senanayake, C. Tetrahedron Lett. 2005, 46, 273.
8. Kamiya, N.; Chikami, Y.; Ishii, Y. Synlett 1990, 675 and references therein.