A convergent synthesis of an LTD4 antagonist, RG12525

Tetrahedron Letters

Volumn 38, Issue 7, 1997, Pages 1129-1132

  Sledeski, Adam W ^a   O'Brien, Michael K ^a   Truesdale, Larry K ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 [4 [2 (5 TETRAZOLYLMETHYL)BENZYLOXY]PHENOXYMETHYL]QUINOLINE; LEUKOTRIENE RECEPTOR BLOCKING AGENT;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0031575570     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02460-4     Document Type: Article

References (23)

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2. b) Huang, F.C.; Galemno, R.A.; Johnson, W.H.; Poli, G.B.; Morrissette, M.M.; Mencel, J.J.; Warus, J.D.; Campbell, H.F.; Nuss, G.W.; Carnathan, G.W.; Van Inwegen, R.G. J. Med. Chem. 1990, 33, 1194.
3. c) Huang, F.C.; Galemno, R.A.; Poli, G.B.; Learn, K.S.; Morrissette, M.M.; Johnson, W.H.; Dankulich, W.P.; Campbell, H.F.; Carnathan, G.W.; Van Inwegen, R.G. J. Med. Chem. 1991, 34, 1704.
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6. 2. a) For discussion of various synthetic approaches to compound 2 see: O'Brien, M.K;, Sledeski, A.W.; Truesdale, L.K. Tetrahedron Letters, in press.
7. b) For recent references on 2-quinolylmethoxyphenyl structural motif in the area of leukotriene biosynthesis inhibitors and leukotriene receptor antagonists see: Kolasa, T.; Gunn, D.E.; Stewart, A.O.; Brooks, C.D.W. Tetrahedron Asymmetry 1996, 7, 2645.
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10. 1H NMR (300 MHz, CDCl3) δ 8.14 (d, 1H), 7.94 (d, 1H), 7.79 (m, 3H), 7.67 9m, 1H), 7.52 (m, 2H), 7.28 (d, 2H), 5.27 (s, 2H), 2.37 (s, 3H).
11. 6. Ratio of tosylate 7 to chloride 8 in the final reaction mixture is highly dependent on the reaction conditions. For a selective preparation of 2-(chloromethyl)quinoline (8) via a similar process see: White, J.D.; Yager, K.M.; Stappenbeck J. Org. Chem. 1993, 58, 3466 and cited references.
12. 3) δ 8.22 (d, 1H), 7.64 (dd, 1H), 7.51 (ddd, 1H), 7.39 (dd, 1H), 7.33 (s, 1H), 7.25 (d, 1H), 6.93 (d, 1h), 3.09 (s, 3H); HRMS calcd. for C12H11N2 (m+1) 183.0922, found 183.0917 (FAB, glycerol). Parent system has been described in: Langry, K.C. J. Org. Chem. 1991, 56, 2400.
13. 8. Stefancich, G.; Artico, M.; Massa, S.; Vomero, S. J. Heterocyclic Chem. 1979, 16, 1443.
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17. 1H NMR (300 MHz, acetone-d6) δ 7.43 (m, 1H), 7.24 (m, 3H), 4.76 (s, 2H), 4.44 (s, 2H).
18. 3) δ 7.43-7.04 (m, 19H), 4.76 (d, J=6.4Hz, 2H), 4.36 (s, 2H), 3.31 (t, J=6.4Hz, 1H, (Q-H)).
19. 3) δ 7.34-7.06 (m, 19H), 4.64 (s, 2H), 4.42 (s, 2H).
20. 14. Corey, E.J.; Kim, C.U.; Takeda, M. Tetrahedron Lett. 1972, 42, 4339.
21. 15. To our knowledge, tetrahydropyranyl group has not been previously used for tetrazole protection.
22. 1H NMR (300 MHz, acetone-d6) δ 7.46 (m, 1H), 7.29 (m, 3H), 4.80 (s, 2H), 4.54 (s, 2H).
23. 17. Ando, T., Yamawaki, J., Kawate, T., Sumi, S., Hanafusa, T. Bull. Chem. Soc. Jpn. 1982, 55, 2505.