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A Concise and Efficient Synthesis of an Impurity, N-Desmethyl Alcaftadine from Alcaftadine: An H1 Antagonist
Corresponding Author(s) : N. Bakthavatchala Reddy
Asian Journal of Chemistry,
Vol. 31 No. 10 (2019): Vol 31 Issue 10
Abstract
Herein, a simple approach for the synthesis of N-desmethyl alcaftadine, an H1 histamine antagonist in solid state and its structure is presented. The reactions were performed under mild and metal free conditions at reflux temperature within a range of 65-70 ºC and the desired product N-desmethyl alcaftadine was obtained in high purity with good yield (96.42 %). It was detected by ultra-high-performance liquid chromatography (UHPLC).
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References
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J.H. Shah, R.M. Hindupur and H.N. Pati, Curr. Bioact. Compd., 11, 170 (2015); https://doi.org/10.2174/1573407211666150910202200.
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T. Gozler, B. Gozler, I. Weiss, A.J. Freyer and M. Shamma, J. Am. Chem. Soc., 106, 6101 (1984); https://doi.org/10.1021/ja00332a069.
H. Li, Y. Wen, F. Wang, P. Wu and X. Wei, Tetrahedron Lett., 56, 5735 (2015); https://doi.org/10.1016/j.tetlet.2015.08.071.
H.S. Chung, P.M. Hon, G. Lin, P.P. But and H. Dong, Planta Med., 69, 914 (2003); https://doi.org/10.1055/s-2003-45100.
H.R. Howard, Expert Opin. Therap. Patents, 15, 1811 (2005); https://doi.org/10.1517/13543776.15.12.1811.
J.P. Hieble, Method of Treating Benign Prostatic Hypertrophy, U.S. Patent 4755507 (2010).
D.M. Wilson, J. Apps, N. Bailey, M.J. Bamford, I.J. Beresford, M.A. Briggs, A.R. Calver, B. Crook, R.P. Davis, S. Davis, D.K. Dean, L. Harris, T.D. Heightman, T. Panchal, C.A. Parr, N. Quashie, J.G.A. Steadman, J. Schogger, S.S. Sehmi, T.O. Stean, A.K. Takle, B.K. Trail, T. White, J. Witherington, A. Worby and A.D. Medhurst, Bioorg. Med. Chem. Lett., 23, 6897 (2013); https://doi.org/10.1016/j.bmcl.2013.09.089.
S.J. Ono and M.B. Abelson, J. Allergy Clin. Immunol., 115, 118 (2005); https://doi.org/10.1016/j.jaci.2004.10.042.
A.I. Graul, E. Cruces, C. Dulsat, E. Arias and M. Stringer, Drugs Today, 48, 33 (2012); https://doi.org/10.1358/dot.2012.48.1.1769676.
S. Yusuf, F. Zhao, S.R. Mehta, S. Chrolavicius, G. Tognoni and K.K. Fox, N. Engl. J. Med., 345, 494 (2001); https://doi.org/10.1056/NEJMoa010746.
H.A. Hageman, Organic Reactions, John Wiley & Sons: New York, vol. 7, Chap. 4 (1953).
J. Santamaria, R. Ouchabane and J. Rigaudy, Tetrahedron Lett., 30, 2927 (1989); https://doi.org/10.1016/S0040-4039(00)99160-3.
J. Santamaria, R. Ouchabane and J. Rigaudy, Tetrahedron Lett., 30, 3977 (1989); https://doi.org/10.1016/S0040-4039(00)99299-2.
S.I. Murahashi, T. Naota, N. Miyaguchi and T. Nakato, Tetrahedron Lett., 33, 6991 (1992); https://doi.org/10.1016/S0040-4039(00)60914-0.
S.I. Murahashi, T. Naota and K. Yonemura, J. Am. Chem. Soc., 110, 8256 (1988); https://doi.org/10.1021/ja00232a060.
I. Monkovic, H. Wong and C. Bachand, Synthesis, 770 (1985); https://doi.org/10.1055/s-1985-31342.
H.Y.P. Choo, Y.O. Shin and J. Park, J. Anal. Toxicol., 14, 116 (1990); https://doi.org/10.1093/jat/14.2.116.
K.C. Rice, J. Org. Chem., 40, 1850 (1975); https://doi.org/10.1021/jo00900a044.
S.W. Baldwin, P.W. Jeffs and S. Natarajan, Synth. Commun., 7, 79 (1977); https://doi.org/10.1080/00397917709410059.
T.A. Montzka, J.D. Matiskella and R.A. Partyka, Tetrahedron Lett., 14, 1325 (1974); https://doi.org/10.1016/S0040-4039(01)82479-5.
R.A. Olofson, J.T. Martz, J.P. Senet, M. Piteau and T. Malfroot, J. Org. Chem., 49, 2081 (1984); https://doi.org/10.1021/jo00185a072.
R.A. Olofson, Pure Appl. Chem., 60, 1715 (1988); https://doi.org/10.1351/pac198860111715.
F.E. Janssens, G.S.M. Diels and J.E. Leenaerts, Imidazo[2,1-b]benzazepine Derivatives, Compositions and Method of Use, U.S. Patent US5468743 A (1995).