Development of an asymmetric synthesis of a chiral quaternary FLAP inhibitor

Journal of Organic Chemistry

Volumn 80, Issue 3, 2015, Pages 1651-1660

  Fandrick, Keith R ^a   Mulder, Jason A ^a   Patel, Nitinchandra D ^a   Gao, Joe ^a   Konrad, Michael ^a,b   Archer, Elizabeth ^a   Buono, Frederic G ^a   Duran, Adil ^a,b   Schmid, Rolf ^a,b   Daeubler, Juergen ^a,b   Desrosiers, Jean Nicolas ^a   Zeng, Xingzhong ^a   Rodriguez, Sonia ^a   Ma, Shengli ^a   Qu, Bo ^a   Li, Zhibin ^a   Fandrick, Daniel R ^a   Grinberg, Nelu ^a   Lee, Heewon ^a   Bosanac, Todd ^a   Takahashi, Hidenori ^a   Chen, Zhidong ^a   Bartolozzi, Alessandra ^a   Nemoto, Peter ^a   Busacca, Carl A ^a   Song, Jinhua J ^a   Yee, Nathan K ^a   Mahaney, Paige E ^a   Senanayake, Chris H ^a   more..

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

^b BOEHRINGER INGELHEIM PHARMA GMBH AND CO KG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANIC COMPOUNDS;

ASYMMETRIC SYNTHESIS; BENZYLIC; BORONATE; BORONIC ESTERS; FORMYLATION; IN-SITU TRAPPING; STEREOGENIC CENTERS; STEREOSPECIFIC;

SYNTHESIS (CHEMICAL);

1 (4 BROMOPHENYL)ETHYL DIISOPROPYLCARBAMATE; 2 (4 BROMOPHENYL) 2 CYCLOPROPYL N' HYDROXYPROPANIMIDAMIDE; 2 [1 (4 BROMOPHENYL) 1 CYCLOPROPYLETHYL] 4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLANE; 2 [4 (2 AMINOPYRIMIDIN 5 YL)PHENYL] 2 CYCLOPROPYL N' HYDROXYPROPANIMIDAMIDE; 2 [4 [3 [1 [4 (2 AMINOPYRIMIDIN 5 YL)PHENYL] 1 CYCLOPROPYLETHYL] 1,2,4 OXADIAZOL 5 YL] 1H PYRAZOL 1 YL]N,N DIMETHYLACETAMIDE; 5 [4 [1 [5 (1H PYRAZOL 4 YL) 1,2,4 OXADIAZOL 3 YL] 1 CYCLOPROPYLETHYL]PHENYL]PYRIMIDIN 2 AMINE; ANION; ARACHIDONATE 5 LIPOXYGENASE ACTIVATING PROTEIN INHIBITOR; BORONIC ACID DERIVATIVE; CARBAMIC ACID; ESTER DERIVATIVE; OXIME; UNCLASSIFIED DRUG; BORON DERIVATIVE; CARBAMIC ACID DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; CHLORINATION; DRUG SYNTHESIS; FORMYLATION; REPRODUCIBILITY; TEMPERATURE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

5-LIPOXYGENASE-ACTIVATING PROTEIN INHIBITORS; BORON COMPOUNDS; CARBAMATES; CATALYSIS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84922724573     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo502550h     Document Type: Article

References (58)

1. Bonow, R. O.; Smaha, L. A.; Smith, S. C., Jr.; Mensah, G. A.; Lenfant, C. Circulation 2002, 106, 1602-1605
2. Stock, N. S.; Bain, G.; Zunic, J.; Li, Y.; Ziff, J.; Roppe, J.; Santini, A.; Darlington, J.; Prodanovich, P.; King, C. D.; Baccei, C.; Lee, C.; Rong, H.; Chapman, C.; Broadhead, A.; Lorrain, D.; Correa, L.; Hutchinson, J. H.; Evans, J. F.; Prasit, P. J. Med. Chem. Lett. 2011, 54, 8013-8029
3. Hakonarson, H.; Thorvaldsson, S.; Helgadottir, A.; Gudbjartsson, D.; Zink, F.; Andresdottir, M.; Manolescu, A.; Arnar, D. O.; Andersen, K.; Sigurdsson, A.; Thorgeirsson, G.; Jonsson, A.; Agnarsson, U.; Bjornsdottir, H.; Gottskalksson, G.; Einarsson, A.; Gudmundsdottir, H.; Adalsteinsdottir, A.; Gudmundsson, K.; Kristjansson, K.; Hardarson, T.; Kristinsson, A.; Topol, E. J.; Gulcher, J.; Kong, A.; Gurney, M.; Thorgeirsson, G.; Stefansson, K. J. Am. Med. Assoc. 2005, 293, 2245-2256
4. Tardif, J.-C.; LAllier, P. L.; Ibrahim, R.; Grégoire, J. C.; Nozza, A.; Cossette, M.; Kouz, S.; Lavoie, M.-A.; Paquin, J.; Brotz, T. M.; Taub, R.; Pressacco, J. Cir. Cardiovasc. Imaging 2010, 3, 298-307
5. Bartolozzi, A.; Bosanac, T.; Chen, Z.; De Lombaert, S.; Huber, J.; Lo, H. Y.; Loke, P. L.; Weimin, L.; Morwick, T. M.; Olague, A.; Riether, D.; Tye, H.; Wu, L.; Zindell, R. (Boehringer Ingelheim International GMBH) WO 2012/024150 A1, 2012.
6. Fandrick, K. R.; Gao, J. J.; Mulder, J. A.; Patel, N.; Zeng, X. (Boehringer Ingelheim International GMBH) WO 2013/119751 A1, 2013.
7. Busacca, C. A.; Fandrick, D. R.; Song, J. J.; Senanayake, C. H. Transition Metal Catalysis in the Pharmaceutical Industry. In Applications of Transition Metal Catalysis in Drug Discovery and Development: An Industrial Perspective; Crawley, M. L.; Trost, B. M., Eds.; Wiley: Hoboken, NJ, 2012.
8. Anderson, N. G. Practical Process Research & Development; Academic Press: San Diego, CA, 2000; p 354.
9. Practical Process Development: Current Chemical and Engineering Challenges; Blacker, J.; Williams, M. T., Eds.; RSC Publishing: London, 2011; p 374.
10. Marek, Y. M.; Pasco, M.; Mejuch, T.; Gilboa, N.; Chechik, H.; Das, J. P. J. Am. Chem. Soc. 2014, 136, 2682
11. Wu, J.; Mampreian, D. M.; Hoveyda, A. H. J. Am. Chem. Soc. 2005, 127, 4584-4585
12. Lee, K.-s.; Brown, M. K.; Hird, A. W.; Hoveyda, A. H. J. Am. Chem. Soc. 2006, 128, 7182-7184
13. Martin, D.; Kehrli, S.; dAugustin, M.; Clavier, H.; Mauduit, M.; Alexakis, A. J. Am. Chem. Soc. 2006, 128, 8416-8417
14. Fillion, E.; Wilsily, A. J. Am. Chem. Soc. 2006, 128, 2774-2775
15. Wilsily, A.; Fillion, E. Org. Lett. 2008, 10, 2801-2804
16. Wilsily, A.; Lou, T.; Fillion, E. Synthesis 2009, 12, 2066-2082
17. Wilsily, A.; Fillion, E. J. Org. Chem. 2009, 74, 8583-8594
18. Hrdina, R.; Müller, C. E.; Wende, R. C.; Lippert, K. M.; Benassi, M.; Spengler, B.; Schreiner, P. R. J. Am. Chem. Soc. 2011, 133, 7624-7627
19. Kimura, T.; Yamamoto, N.; Suzuki, Y.; Kawano, K.; Norimine, Y.; Ito, K.; Nagato, S.; Iimura, Y.; Yonaga, M. J. Org. Chem. 2002, 67, 6228-6231
20. Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. J. Am. Chem. Soc. 1997, 119, 11224-11235
21. Stymiest, J. L.; Bagutski, V.; French, R. M.; Aggarwal, V. K. Nature 2008, 456, 778-782
22. Bagutski, V.; Ros, A.; Aggarwal, V. K. Tetrahedron 2009, 65, 9956-9960
23. Bagutski, V.; French, R. M.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2010, 49, 5142-5145
24. Sonawane, R. P.; Jheengut, V.; Rabalakos, C.; Larouche-Gauthier, R.; Scott, H. K.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2011, 50, 3760-3763
25. Rangaishenvi, M. V.; Singaram, B.; Brown, H. C. J. Org. Chem. 1991, 56, 3286-3294
26. Scott, H. K.; Aggarwal, V. K. Chem. Eur. J. 2011, 17, 13124-13132
27. Farina, V.; Reeves, J. T.; Senanayake, C. H.; Song, J. J. Chem. Rev. 2006, 106, 2734-2793
28. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483
29. Stanforth, S. P. Tetrahedron 1998, 54, 263-303
30. Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633-9695
31. Bellina, F.; Carpita, A.; Rossi, R. Synthesis 2004, 14, 2419-2440
32. Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521-2522
33. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102
34. Blacker, J. A.; Thompson, P. Scale-up Studies in Asymmetric Transfer Hydrogenation. In Asymmetric Catalysis on Industrial Scale, 2 nd ed.; Blaser, H.-U.; Schmidt, E., Eds.; Wiley: Hoboken, NJ, 2010; pp 265-290.
35. Hoppe, D.; Hintze, F.; Tebben, P. Angew. Chem., Int. Ed. Engl. 1990, 29, 1422-1424
36. Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2282-2316
37. Matteson, D. S.; Soundararajan, R.; Ho, O. C.; Gatzweiler, W. Organometallics 1996, 15, 152-163
38. Fandrick, K. R.; Patel, N. D.; Mulder, J. A.; Gao, J.; Konrad, M.; Archer, E.; Buono, F. G.; Duran, A.; Schmid, R.; Daeubler, J.; Fandrick, D. R.; Ma, S.; Grinberg, N.; Lee, H.; Busacca, C. A.; Song, J.; Yee, N. K.; Senanayake, C. H. Org. Lett. 2014, 16, 4360-4364
39. Matteson, D. S.; Man, H.-W.; Ho, O. C. J. Am. Chem. Soc. 1996, 118, 4560-4566
40. Matteson, D. S.; Soundararajan, R.; Ho, O. C.; Gatzweiler, W. Organometallics 1996, 15, 152-163
41. During the scaling of the DCM homologation, a similar process was reported: Pulis, A. P.; Aggarwal, V. K. J. Am. Chem. Soc. 2012, 134, 7570-7574.
42. Grabarnick, M.; Zamir, S. Org. Process Res. Dev. 2003, 7, 237-243
43. Connolly, T. J.; Matchett, M.; McGarry, P.; Sukhtankar, S.; Zhu, J. Org. Process Res. Dev. 2006, 10, 391-397
44. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
45. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
46. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650-654
47. McLean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639-5648
48. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision D.01; Gaussian, Inc., Wallingford, CT, 2009.
49. Liu, K.-C.; Shelton, B. R.; Howe, R. K. J. Org. Chem. 1980, 45, 3916-3918
50. Menzel, K.; Machrouhi, F.; Bodenstein, M.; Alorati, A.; Cowden, C.; Gibson, A. W.; Bishop, B.; Ikemoto, N.; Nelson, T. D.; Kress, M. H.; Frantz, D. E. Org. Process Res. Dev. 2009, 13, 519-524
51. Hansen, E. C.; Levent, M.; Connolly, T. J. Org. Process Res. Dev. 2010, 14, 574-578
52. Miyaura, N.; Yamada, K.; Suzuki, A. Tetrahedron Lett. 1979, 20, 3437-3440
53. Miyaura, N.; Suzuki, A. Chem. Commun. 1979, 19) 866-867
54. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95 (7) 2457-2483
55. Busacca, C. B.; Eriksson, M. C.; Haddad, N.; Han, Z. S.; Lorenz, J. C.; Qu, B.; Zeng, X.; Senanayake, C. H. Org. Synth. 2013, 90, 316-326
56. Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224-3225
57. Qu, B.; Haddad, N.; Han, Z. S.; Rodriguez, S.; Lorenz, J. C.; Grinberg, N.; Lee, H.; Busacca, C. A.; Krishnamurthy, D. K.; Senanayake, C. H. Tetrahedron Lett. 2009, 50, 6126-6129
58. Kayukova, L. A. Pharm. Chem. J. 2005, 39, 539-547