Aminocarbonylation route to tolvaptan

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 23, 2007, Pages 6455-6458

  Torisawa, Yasuhiro ^a   Furuta, Takuya ^b   Nishi, Takao ^b   Aki, Shinji ^b   Minamikawa, Jun ichi ^b  

^a TAKASAKI UNIVERSITY OF HEALTH AND WELFARE   (Japan)

^b OTSUKA PHARMACEUTICAL CO LTD   (Japan)

Author keywords

Carbonylation; Cesium salt; DBU; Palladium; Vasopressin

Indexed keywords

ARYL BROMIDE; BENZAZEPINE DERIVATIVE; NH BENZAZEPINONE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TOLVAPTAN; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; DRUG STRUCTURE; DRUG SYNTHESIS;

BENZAZEPINES; CATALYSIS; CHEMISTRY, PHARMACEUTICAL; PALLADIUM; VASOPRESSINS;

EID: 35649007351     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.09.094     Document Type: Article

References (12)

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2. Blakeney J.S., Reid R.C., Le G.T., and Fairlie D.P. Chem. Rev. 107 (2007) 2960
3. See as a general review. Li J.J., and Gribble G.W. Palladium in Heterocyclic Chemistry (2000), Pergamon, Amsterdam
4. Mori M. In: Negishi E.-I. (Ed). Handbook of Organopalladium Chemistry for Organic Synthesis Vol. 2 (2002), Wiley, New York 2313-2332
5. Torisawa Y., Nishi T., and Minamikawa J. Bioorg. Med. Chem. Lett 10 (2000) 2493 and references therein
6. Kubota Y., Hanaoka T., Takeuchi K., and Sugi Y. Synlett (1994) 515
7. See as an example of base selection:. Atkins R.J., Banks A., Bellingham R.K., Breen G.F., Carey J.S., Etridge S.K., Hayes J.F., Hussain N., Morgan D.O., Oxley P., Passey S.C., Walsgrove T.C., and Wells A.S. Org. Process Res. Dev. 7 (2003) 663
8. Wan Y., Alterman M., Larhed M., and Hallberg A. J. Org. Chem. 67 (2002) 6232
9. 2 column chromatography to afford the desired amide product (81-85%) with 99.1% purity as judged by HPLC.
10. Wannberg J., and Larhed M. J. Org. Chem. 68 (2003) 5750
11. Yamazaki K., and Kondo Y. J. Comb. Chem. 6 (2004) 121
12. Our preliminary survey has indicated that attempted carbonylation of 2 with various metal carbonyl derivatives according to Ref. 9 and 10 gave rather unsatisfactory results (product yields were mostly less than 40%). We also observed that hydroxycarbonylation was faster (prevailed) with reported metal carbonyl derivatives rather than aminocarbonylation (under normal heating conditions).