Synthesis of angiotensin II receptor blockers by means of a catalytic system for C-H Activation

Journal of Organic Chemistry

Volumn 76, Issue 24, 2011, Pages 10198-10206

  Seki, Masahiko ^a   Nagahama, Masaki ^a  

^a API Corporation   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANGIOTENSIN II; C-H ACTIVATION; CATALYTIC SYSTEM; REACTION MIXTURE; SELECTED METALS;

ACTIVATION ANALYSIS; RUTHENIUM; RUTHENIUM COMPOUNDS;

SYNTHESIS (CHEMICAL);

ALCOHOL; BIPHENYL; BROMIDE; CARBON; HYDROGEN; LOSARTAN; METAL; RUTHENIUM; SCAVENGER; TRIPHENYLPHOSPHINE; VALSARTAN; WATER;

ALKYLATION; ARTICLE; BIOPHENYLATION; BROMINATION; CARBON HYDROGEN BOND; CATALYSIS; CHEMICAL BOND; CHEMICAL MODIFICATION; CRYSTALLIZATION; DEPROTECTION REACTION; DRUG SYNTHESIS; GREEN CHEMISTRY; HYDROGENATION;

ANGIOTENSIN RECEPTOR ANTAGONISTS; ANTIHYPERTENSIVE AGENTS; BIPHENYL COMPOUNDS; CATALYSIS; CHELATING AGENTS; HUMANS; LOSARTAN; MAGNETIC RESONANCE SPECTROSCOPY; RUTHENIUM; TETRAZOLES; TETRAZOLIUM SALTS; VALINE;

EID: 84055200105     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo202041e     Document Type: Article

References (97)

1. (a) Yasuda, N. In The Art of Process Chemistry; Wiley VCH: Weinheim, 2011.
2. (b) Anderson, N. G. In Practical Process Research & Development; Academic Press: Oxford, 2000.
3. (c) Dunn, P.; Wells, A.; Williams, M. T. In Green Chemistry in the Pharmaceutical Industry; Wiley-VCH: Weinheim, 2010.
4. see: (a) Daugulis, O.; Do, J.-Q.; Shabashov, D. Acc. Chem. Res. 2009, 42, 1074.
5. (b) Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094.
6. (c) Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792.
7. (d) Willis, M. C. Chem. Rev. 2010, 110, 725.
8. (e) Mkhalid, I. A. I.; Barnard, J. H.; Marder, T. B.; Murphy, J. M.; Hartwig, J. F. Chem. Rev. 2010, 110, 890.
9. (f) Ackermann, L. Chem. Commun. 2010, 46, 4866.
10. (g) Dudnik, A. S.; Gevorgyan, V. Angew. Chem, Int. Ed. 2010, 49, 2096.
11. (h) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.
12. (i) Sun, S.-L.; Li, B.-J.; Shi, Z.-J. Chem. Commun. 2010, 46, 677.
13. (j) Peng, H. M.; Dai, L.-X.; You, S.-L. Angew. Chem., Int. Ed. 2010, 49, 5826.
14. (k) Ackermann, L. Chem. Rev. 2011, 111, 1315.
15. see: (a) Oi, S.; Fukita, S.; Hirata, N.; Watanuki, N.; Miyano, S.; Inoue, Y. Org. Lett. 2001, 3, 2579.
16. (b) Martinez, R.; Chevalier.; Darses, S.; Genet, J.-P. Angew. Chem., Int. Ed. 2006, 45, 8232.
17. (c) Ackermann, L.; Althammer, A.; Born, R. Synlett 2007, 2833.
18. (d) L. Ackermann, L.; A. Althammer, A.; R. Born, R. Tetrahedron 2008, 64, 6115.
19. (e) Cheng, K.; Yao, B.; Zhao, J.; Zhang, Y. Org. Lett. 2008, 10, 5309.
20. (f) Ozdemir, I.; Demir, S.; Cetinkaya, B.; Gourlaouen, C.; Maseras, F.; Bruneau, C.; Dixneuf, P. H. J. Am. Chem. Soc. 2008, 130, 1156.
21. (g) Ackermann, L.; Vicente, R.; Althammer, A. Org. Lett. 2008, 10, 2299.
22. (h) Oi, S.; Funayama, R.; Hattori, T.; Inoue, Y. Tetrahedron 2008, 64, 6051.
23. (i) Ackermann, L.; Born, R.; Vicente, R. ChemSusChem 2009, 2, 546.
24. (j) Ackermann, L.; Novak, P. Org. Lett. 2009, 11, 4966.
25. (k) Martinez, R.; Simon, M.-O.; Chevalier, R.; Pautigny, C.; Genet, J.-P.; Darses, S. J. Am. Chem. Soc. 2009, 131, 7887.
26. (l) Požgan, F.; Dixneuf, P. H. Adv. Synth. Catal. 2009, 351, 1737.
27. (m) Ackermann, L.; Novák, P.; Vicente, R; Hofmann, N. Angew. Chem., Int. Ed. 2009, 48, 6045.
28. (n) Martinez, R.; Simon, M.-O.; Chevalier, R.; Pautigny, C; Genet, J.-P.; Darses, S. J. Am. Chem. Soc. 2009, 131, 7887.
29. (o) Inoue, S.; Shiota, H.; Fukumoto, Y.; Chatani, N. J. Am. Chem. Soc. 2009, 131, 6898.
30. (p) Miura, H.; Wada, K.; Hosokawa, S.; Inoue, M. Chem.-Eur. J. 2010, 16, 4186.
31. (q) Arockiam, P. B.; Fischmeister, C; Bruneau, C; Dixneuf, P. H. Angew. Chem., Int. Ed. 2010, 49, 6629.
32. (r) Ackermann, L.; Novak, P.; Vicente, R.; Pirovano, V; Potukuchi, H. K. Synthesis 2010, 2245.
33. (s) Simon, M.-O.; Genet, J.-P.; Darses, S. Org. Lett. 2010, 12, 3038.
34. (t) Ackermann, L.; Vicente, R; Potukuchi, H. K.; Pirovano, V Org. Lett. 2010, 12, 5032.
35. (u) Ouellet, S. G; Roy, A.; Molinaro, C.; Angelaud, R; Marcoux, J.-F.; O'Shea, P. D.; Davies, I. W. J. Org. Chem. 2011, 76, 1436.
36. (v) Flegeau, E. F.; Bruneau, C.; Dixneuf, P. H.; Jutand, A. J. Am. Chem. Soc. 2011, 133, 10161.
37. (w) Ackermann, L.; Lygin, A. V Org. Lett. 2011, 13, 3332.
38. (x) Li, B.; Bheeter, C. B.; Darcel, C.; Dixneuf, P. H. ACS Catal. 2011, 1, 1221.
39. (y) Lakshman, M. K.; Deb, A. C.; Chamala, R R; Pradhan, P.; Pratap, R Angew. Chem., Int. Ed. 2011, DOI: 10.1002/anie.201104035.
40. see: (a) Chiong, H. A.; Pham, Q.-N.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 9879.
41. (b) Wang, X.; Gribkov, D. V; Sames, D. J. Org. Chem. 2007, 72, 1476.
42. (c) Glri, R; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 14082.
43. (d) Mei, T.-S.; Giri, R; Maugel, N; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 5215.
44. (e) Brasche, G; Garcia-Fortanet, J.; Buchwald, S. L. Org. Lett. 2008, 10, 2207.
45. (f) Zhao, D.; Wang, W.; Lian, S.; Yang, F.; Lan, J.; You, J. Chem.-Eur. J. 2009, 15, 1337.
46. (g) Campeau, L.-C.; Staurt, D. R; Leclerc, J.-P.; Bertrand-Laperte, M.; Villemure, E.; Sun, H.-Y.; Lasserre, S.; Guimond, N; Lecavallier, M.; Fagnou, K. J. Am. Chem. Soc. 2009, 131, 3291.
47. (h) Lapointe, D.; Fagnou, K. Org. Lett. 2009, 11, 4160.
48. (i) Powers, D. C.; Geibel, M. A. L.; Klein, J. E. M. N; Ritter, T. J. Am. Chem. Soc. 2009, 131, 17050.
49. (j) Laidaoui, N; Miloudi, A; El Abed, D.; Doucet, H. Synthesis 2010, 2553.
50. (k) Li, M.; Ge, H. Org. Lett. 2010, 12, 3464.
51. (l) Mukai, T.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2010, 12, 1360.
52. (m) Huang, J.; Chan, J.; Chen, Y.; Borths, C. J.; Baucom, K. D.; Larsen, R D.; Faul, M. M. J. Am. Chem. Soc. 2010, 132, 3674.
53. (n) Xian, B.; Fu, Y.; Xu, J.; Gong, T.-J.; Dai, J.-J.; Yi, J.; Liu, L. J. Am. Chem. Soc. 2010, 132, 468.
54. (o) X, P.; Yang, F.; Qin, S.; Zhao, D.; Lan, J.; Gao, G; Hu, C.; You, J. J. Am. Chem. Soc. 2010, 132, 1822.
55. (p) Ackermann, L.; Barfusser, S.; Pospech, J. Org. Lett. 2010, 12, 724.
56. (q) Simon, M.-O.; Genet, J.-P.; Darses, S. Org. Lett. 2010, 12, 3038.
57. (r) Zhang, S.; Luo, F.; Wang, W.; Jia, X.; Hu, M.; Cheng, J. Tetrahedron Lett. 2010, 51, 3317.
58. (s) Bedford, R B.; Mitchel, C. J.; Webster, R L. Chem. Commun. 2010, 46, 3095.
59. (t) Song, B.; Zheng, X.; Mo, J.; Xu, B. Adv. Synth. Catal. 2010, 352, 329.
60. (u) Roy, D.; Mom, S.; Beauperin, M.; Doucet, H.; Hierso, J.-C. Angew. Chem., Int. Ed. 2010, 49, 6650.
61. (v) Wasa, M.; Worrel, B. T.; Yu, J.-Q. Angew. Chem., Int. Ed. 2010, 49, 1275.
62. (w) Nishikata, T.; Abela, A. R; Lipshutz, B. H. Angew. Chem., Int. Ed. 2010, 49, 781.
63. (x) Potavathri, S.; Pereira, K. C.; Gorelsky, S. I.; Pike, A.; LeBris, A. P.; DeBoef, B. J. Am. Chem. Soc. 2010, 132, 14676.
64. (y) Feng, Y.; Wang, Y.; Landgraf, B.; Liu, S.; Chen, G. Org. Lett. 2010, 12, 3414.
65. (z) Wang, X.; Leow, D.; Yu, J.-Q. J. Am. Chem. Soc. 2011, 133, 13864.
66. (aa) Yichen Tan, Y.; Hartwig, J. F. J. Am. Chem. Soc. 2011, 133, 3308.
67. (bb) Li, W.; Xu, Z.; Sun, P.; Jiang, X.; Fang, M. Org. Lett. 2011, 13, 1286.
68. (cc) Guo, H.-M.; Jiang, L.-L.; Niu, H.-Y.; Rao, W.-H; Liang, L.; Mao, R-Z.; Li, D.-Y.; Qu, G.-R Org. Lett. 2011, 13, 2008.
69. (dd) Lyons, T. W.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2011, 133, 4455.
70. (ee) Zhou, J.; He, J.; Wang, B.; Yang, W.; Hongjun Ren, H. J. Am. Chem. Soc. 2011, 133, 6868.
71. (ff) Xiao, F.; Shuai, Q.; Zhao, F.; Basl, O.; Deng, G.; Li, C.-J. Org. Lett. 2011, 13, 1614.
72. (gg) Guo, H.-M.; Jiang, L.-L.; Niu, H. Y.; Rao, W.-H.; Liang, Mao, R-Z.; Li, D.-Y.; Qu, G.-R Org. Lett. 2011, 13, 2008.
73. (a) Carini, D. J.; Duncia, J. V; Aldrich, P. E.; Chiu, A T.; Johnson, A L.; Pierce, M. E.; Price, W. A; Santella, J. B. III; Wells, G. J. J. Med. Chem. 1991, 34, 2525.
74. (b) Kubo, K.; Kohara, Yoshimura, Y.; Inada, Y.; Shibouta, Y.; Furukawa, Y.; Kato, T.; Nishikawa, K.; Naka, T. J. Med. Chem. 1993, 36, 2343.
75. (c) Bernhart, C. A.; Perreaut, P. M.; Ferrari, B. P.; Muneaux, Y. A.; A Assens, J. L. A.; Clement, J.; Haudricourt, F.; Muneaux, C. F.; Taillades, J. E. J. Med. Chem. 1993, 36, 3371.
76. (d) Wexler, R R; Greenlee, W. J.; Irvin, J. D.; Goldberg, M. R.; Prendergast, K.; Smith, R. D.; Timmermans, P. B. M. W. M. J. Med. Chem. 1996, 39, 625.
77. (a) Larsen, R. D.; King, A. O.; Chen, C. Y.; Corley, E. G.; Foster, B. S.; Roberts, F. E.; Yang, C.; Lieberman, D. R.; Reamer, R. A.; Tschaen, D. M.; Verhoeven, T. R.; Reider, P. J.; Lo, Y. S.; Rossano, L. T.; Brookes, S.; Meloni, D.; Moore, J. R.; Arnett, J. F. J. Org. Chem. 1994, 59, 6391.
78. (b) Beutler, U.; Boehm, M.; Fuenfschilling, P. C.; Heinz, T.; Mutz, J.-P.; Onken, U.; Mueller, M.; Zaugg, W. Org. Process Res. Dev. 2007, 11, 892.
79. (c) Kumar, N.; Reddy, S. B.; Sinha, B. K.; Mukkanti, K.; Dandala, R. Org. Process Res. Dev. 2009, 13, 1185.
80. (d) Wang, G.-X.; Sun, B.-P.; Peng, C.-H. Org. Process Res. Dev. 2011, 15, 986.
81. see: Seki, M. ACS Catal. 2011, 1, 607.
82. Hiroshima, S.; Matsumura, D.; Kochi, T.; Kakiuchi, F. Org. Lett. 2010, 12, 5318.
83. (a) Mihina, J. S.; Herbst, R. M. J. Org. Chem. 1950, 15, 1082.
84. (b) Katritzky, A. R.; Cai, C.; Meher, N. K. Synthesis 2007, 1204.
85. P. S. Hallman, P. S.; Stephenson, T. A.; Wilkinson, G. Inorg. Synth. 1970, 12, 237.
86. Wassenaar, J.; Jansen, E.; van Zeist, W.-J.; Bickelhaupt, F. M.; Siegler, M. A.; Spek, A. L.; Reek, J. N. H. Nat. Chem. 2010, 2, 417.
87. Martinez, R.; Simon, M.-O.; Chevalier, R.; Pautigny, C.; Genet, J.-P.; Darses, S. J. Am. Chem. Soc. 2009, 131, 7887.
88. (a) Kuwano, R.; Yokogi, M. Chem Commun. 2005, 5899.
89. (b) Yokogi, M.; Kuwano, R. Tetrahedron Lett. 2007, 48, 6109.
90. Kumar, K. V.; Dhirenkumar, M.; Sanjay, N., V.; Vijaykumar, D., L., L. Teva Pharmaceutical Industries Ltd., WO2008/027385A2.
91. Garcia-Cuadrado, D.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2006, 128, 1066.
92. see: (a) Naud, F.; Spindler, F.; Rueggeberg, C. J.; Schmidt, A. T.; Blaser, H.-U. Org. Process Res. Dev. 2007, 11, 519.
93. (b) Armstrong, D. J.; Goto, Y.; Hashihayata, T.; Kato, T.; Kelly, M. J. III; Layton, M. E.; Lindsley, C. W.; Ogino, Y.; Onozaki, Y. Rodzinak, K. J.; Rossi, M. A.; Sanderson, P. E.; Wang, J.; Yaroschak, M. Merck Sharp & Dohme, Banyu Pharma Co. Ltd, WO2010088177A1.
94. (c) Liu, K.; Stachel, S. J.; Coburn, C. A.; Steele, T. G.; Soll, R.; Wu, H.; Peng, X.; Cai, Y.; Du, X.; Li, J. Merck Sharp & Dohme, WO2010094242 A1.
95. (a) Buckle, D. R.; Rockell, C. J. M. J. Chem. Soc., Perkin 1 1982, 627.
96. (b) Chida, N.; Ohtsuka, M.; Ogawa, S. J. Org. Chem. 1993, 58, 4441.
97. Seko, T.; Katsumata, S.; Kato, M.; Manako, J. Ono Pharmaceutical Co., Ltd., WO03030937 A1.