Efficient synthesis of 1,4-diaryl-5-methyl-1,2,3-triazole, a potential mglur1 antagonist, and the risk assessment study of arylazides

Organic Process Research and Development

Volumn 13, Issue 6, 2009, Pages 1407-1412

  Tsuritani, Takayuki ^a   Mizuno, Hiroo ^a   Nonoyama, Nobuaki ^a   Kii, Satoshi ^a   Akao, Atsushi ^a   Sato, Kimihiko ^a   Yasuda, Nobuyoshi ^b   Mase, Toshiaki ^a  

^a BANYU PHARMACEUTICAL CO LTD   (Japan)

^b MERCK RESEARCH LABORATORIES   (United States)

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EID: 72449206576     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op900062p     Document Type: Article

References (31)

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2. (b) Suzuki, G.; Kimura, T.; Satow, A.; Kaneko, N.; Fukuda, J.; Hikichi, H.; Sakai, N.; Maehara, S.; Kawagoe-Takaki, H.; Hata, M.; Azuma, T.; Ito, S.; Kawamoto, H.; Ohta, H. J. Pharmacol. Exp. Ther. 2007, 321, 1144, and references cited therein.
3. (a) Ohta, H.; Sato, A.; Kimura, T.; Suzuki, G.; Kawamoto, H. PCT Int. Appl. WO 2007007909 A1 20070118, 2007.
4. (b) Kawamoto, H.; Ito, S.; Satoh, A.; Nagatomi, Y.; Hirata, Y.; Kimura, T.; Suzuki, G.; Sato, A.; Ohta, H. PCT Int. Appl. WO 2005085214 A1 20050915, 2005.
5. Tsuritani, T.; Kii, S.; Akao, A.; Sato, K.; Nonoyama, N.; Mase, T.; Yasuda, N. Synlett 2006, 801.
6. 3-catalyzed aminolysis of lactone, see: Lesimple, P.; Bigg, D. C. H. Synthesis 1991, 306.
7. (a) Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; pp 1-176.
8. (b) Padwa, A. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol.4, pp 1069-1109.
9. (c) Fan, W.-Q.; Katritzky, A. R. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; Vol.4, pp 101-126.
10. Boyer, J. H.; Moriarty, R.; de Darwent, B.; Smith, P. A. S. Chem. Eng. News 1964, 42, 6.
11. Lindsay, R. O.; Allen, C. F. H. Org. Synth. 1942, 22, 96.
12. All arylazides were synthesized with Sandmeyer reaction from the corresponding arylamines.
13. Burelbach, J. P.; Miller, A. E. Proc. NATAS Annu. Conf. Therm. Anal. Appl. 2001, 29, 567.
14. Odlo, K.; Hentzen, J.; dit Chabert, J. F.; Ducki, S.; Gani, O. A.; Sylte, I.; Skrede, M.; Florenes, V. A.; Hansen, T. V. Bioorg. Med. Chem. 2008, 16, 4829.
15. Iranpoor, N.; Firouzabadi, H.; Nowrouzi, N. Tetrahedron Lett. 2008, 49, 4242.
16. Jacob, A.; Ulf, M.; Fredrik, B.; Xifu, L. Synlett 2005, 2209.
17. The obtained 2,4-difluorophenyazide (5) was labile against oxygen and light. The solution of azide 5 took on deep black color unless it was stored under light shielding, nitrogen atmosphere and low temperature. For the photochemistry of fluorinated aryl azides, see: Leyva, E.; Munoz, D.; Platz, M. S. J. Org. Chem. 1989, 54, 5938.
18. (a) Krasiñski, A.; Fokin, V. V.; Sharpless, K. B. Org. Lett. 2004, 6, 1237.
19. (b) Akimova, G. S.; Chistokletov, V. N.; Petrov, A. A. Zh. Org. Khim. 1967, 3, 968.
20. (c) Akimova, G. S.; Chistokletov, V. N.; Petrov, A. A. Zh. Org. Khim. 1967, 3, 2241.
21. (d) Akimova, G. S.; Chistokletov, V. N.; Petrov, A. A. Zh. Org. Khim. 1968, 4, 389.
22. The reactions of the resulting 4-magnesiotriazole 3-Mg with various electrophiles has already reported by Sharpless (ref 14); however, the transition metal-catalyzed reactions of 3-Mg with arylhalides were unexplored.
23. For detailed information of this one-pot coupling reaction, see: Akao, A.; Tsuritani, T.; Kii, S.; Sato, K.; Nonoyama, N.; Mase, T.; Yasuda, N. Synlett 2007, 31.
24. The addition of the sodium nitrite aqueous solution should be controlled with stirring and cooling throughout due to the moderate size of heat generation,-18.6 kcal/mol (aniline) of aniline with an adiabatic temperature rise of +6.4 K.
25. 3 could pose a thermal hazard. Therefore, it is recommended to prepare a more dilute sodium azide aqueous solution, the temperature of the sodium azide aqueous solution must be maintained cold,-5 °C to avoid volatilization of hydrogen azide (boiling point of hydrogen azide is 36-38 °C), and the addition of the sodium azide aqueous solution should be controlled with stirring and cooling throughout due to the moderate size of heat generation,- 52.0 kcal/mol (aniline) of aniline with an adiabatic temperature rise of + 17.0 K. The appropriate venting capacity must be calculated to deal with nitrogen gas generation during addition of sodium azide aqueous solution.
26. The aqueous waste before aqueous NaOH wash operations must be treated by aqueous NaOH.
27. The batch temperature during the concentration must be kept as low as possible and not approach temperatures above 40 °C as there is a large exotherm present in the concentrate. A high alarm set at 50 °C should be provided for the reactor. Emergency cooling should be applied if the alarm goes off. Dilution of batch with cold MTBE is to be done if the batch temperature approaches 70 °C. The product solution may not be concentrated to a level significantly higher than that tested (29.4 wt % MTBE solution).
28. The addition of MTBE solution of arylazide 5 to the vessel should be controlled with stirring and cooling throughout. The heat release was measured to be-37.1 kcal/mol (azide) of the arylazide with an adiabatic temperature rise of +32.9 K. A high temperature alarm of 50 °C should be set on the reactor.
29. 2 (1300 g) was added keeping the temperature range between 20 to 30 °C. To the solution, molecular sieves 4 Å (1300 g) was added. The resultant solution was left at rest for overnight at ambient temperature, and its supernatant solution was used for the coupling reaction.
30. The addition of zinc chloride THF solution to the vessel should be controlled with stirring and cooling throughout. The heat release was measured to be-8.4 cal/g (batch) with an adiabatic temperature rise of +19.9 K.
31. The addition of 1 N HCl to the vessel should be controlled with stirring and cooling throughout. The heat release was measured to be-5.6 cal/g (batch) with an adiabatic temperature rise of +9.5 K.