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A Convenient Way to Prepare the Key Intermediate 3-Aminomethyl-3-methyl-4-(metho-xyimino)pyrrolidine Dihydrochloride of DW286, a New Naphthyridone Antibacterial
Corresponding Author(s) : Ming-Liang Liu
Asian Journal of Chemistry,
Vol. 25 No. 4 (2013): Vol 25 Issue 4
Abstract
We report herein a convenient way to prepare the key intermediate 3-aminomethyl-3-methyl-4-(methoxyimino)pyrrolidine dihydrochloride of DW286, a new fluoronaphthyridone antibacterial agent, via a 4-step sequence in an overall yield of 56 %. In this procedure, it was crucial that selective reduction of the cyano group of the cyano ketone (5) was done successfully using 5 % Pd/C as the catalytic hydrogenation.
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- H.S. Park, S.J. Sung, D.R. Choi and J.K. Kwak, Int. J. Antimicrob. Agents, 36, 230 (2010).
- H.J. Yun, Y.H. Min, Y.W. Jo, M.J. Shim and E.C. Choi, Int. J. Antimicrob. Agents, 25, 334 (2005).
- M.J. Kim, H.J. Yun, J.W. Kang, S. Kim, J.H. Kwak and E.C. Choi, Antimicrob. Chemother., 51, 1011 (2003).
- H.J. Yun, Y.H. Min, J.A. Lim, J.W. Kang, S.Y. Kim, M.J. Kim, J.H. Jeong, Y.J. Choi, H.J. Kwon, Y.H. Jung, M.J. Shim and E.C. Choi, Antimicrob. Agents Chemother., 46, 3071 (2002).
- M.J. Suto, J.M. Domagala, G.E. Roland, G.B. Mailloux and M.A. Cohen, J. Med. Chem., 35, 4745 (1992).
- D.R. Choi, J.H. Shin, J. Yang, S.H. Yoon and Y.H. Jung, Bioorg. Med. Chem. Lett., 14, 1273 (2004).
- L.S. Feng, M.L. Liu, Y.B. Zhang, et al., Chem. Res. Chin. Univ., 27, 981 (2011).
References
H.S. Park, S.J. Sung, D.R. Choi and J.K. Kwak, Int. J. Antimicrob. Agents, 36, 230 (2010).
H.J. Yun, Y.H. Min, Y.W. Jo, M.J. Shim and E.C. Choi, Int. J. Antimicrob. Agents, 25, 334 (2005).
M.J. Kim, H.J. Yun, J.W. Kang, S. Kim, J.H. Kwak and E.C. Choi, Antimicrob. Chemother., 51, 1011 (2003).
H.J. Yun, Y.H. Min, J.A. Lim, J.W. Kang, S.Y. Kim, M.J. Kim, J.H. Jeong, Y.J. Choi, H.J. Kwon, Y.H. Jung, M.J. Shim and E.C. Choi, Antimicrob. Agents Chemother., 46, 3071 (2002).
M.J. Suto, J.M. Domagala, G.E. Roland, G.B. Mailloux and M.A. Cohen, J. Med. Chem., 35, 4745 (1992).
D.R. Choi, J.H. Shin, J. Yang, S.H. Yoon and Y.H. Jung, Bioorg. Med. Chem. Lett., 14, 1273 (2004).
L.S. Feng, M.L. Liu, Y.B. Zhang, et al., Chem. Res. Chin. Univ., 27, 981 (2011).