Experimental and computational study of intermolecular migration of N,N-dimethylcarbamoyl group from N(7) to N(1) on a 7-azaindoline derivative |
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| Authors: | Yoshiharu Uruno Akio Tanaka Kazuki Hashimoto Shinya Usui Yasunao Inoue Yasuko Konishi Atsushi Suwa Kentaro Takai Wataru Katoda Norio Fujiwara Takaaki Sumiyoshi |
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| Affiliation: | 1. Drug Research Division, Dainippon Sumitomo Pharma Co. Ltd., 33-94 Enoki-cho, Suita, Osaka 564-0053, Japan;2. Organic Synthesis Research Laboratory, Sumitomo Chemical Co. Ltd., 1-98, Kasugade-naka 3-chome, Konohana-ku, Osaka 554-8558, Japan;3. Process Chemistry Research & Development Laboratories, Dainippon Sumitomo Pharma Co. Ltd., 1-98, Kasugade-naka 3-chome, Konohana-ku, Osaka 554-8558, Japan;4. R & D Department, DSP Gokyo Food & Chemical Co. Ltd., 33-94 Enoki-cho, Suita, Osaka 564-0053, Japan |
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| Abstract: | N,N-Dimethylcarbamoylation of the anilinic nitrogen atom N(1) on the spiro 7-azaindoline consists of two steps. The first step is N,N-dimethylcarbamoylation of the pyridyl nitrogen atom N(7), leading to the formation of an isolable intermediate. The second step is intermolecular migration of the N,N-dimethylcarbamoyl group from the pyridyl nitrogen atom N(7) to the anilinic nitrogen atom N(1). We accomplished optimization of the reaction conditions based on the revealed reaction mechanism and a large scale synthesis of compound 3 in quantitative yield. |
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| Keywords: | 7-Azaindoline N,N-Dimethylcarbamoylation Intermolecular migration Muscarinic acetylcholine receptors agonist DFT calculation |
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