The alkylation of Diphenylacetonitrile [86-29-3] (1)[7] with 1,2-dibromoethane (2) gives 4-Bromo-2,2-Diphenylbutyronitrile [39186-58-8] (3). Alkylation with 2-Methylimidazole (4) gives 4-(2-Methyl-1H-imidazol-1-yl)-2,2-diphenylbutanenitrile [214777-43-2] (5). Partial hydrolysis of the nitrile to the amide completes the synthesis of Imidafenacin (6).
References
^Kobayashi F, Yageta Y, Segawa M, Matsuzawa S (2007). "Effects of imidafenacin (KRP-197/ONO-8025), a new anti-cholinergic agent, on muscarinic acetylcholine receptors. High affinities for M3 and M1 receptor subtypes and selectivity for urinary bladder over salivary gland". Arzneimittelforschung. 57 (2): 92–100. doi:10.1055/s-0031-1296589. PMID17396619.
^Miyachi, Hiroyuki; Kiyota, Hiromi; Segawa, Mitsuru (1999). "Design, synthesis and antimuscarinic activity of some imidazolium derivatives". Bioorganic & Medicinal Chemistry Letters. 9 (20): 3003–3008. doi:10.1016/S0960-894X(99)00517-X.
^Yuuji Ishiguro, Yasuhiro Aizawa, Masahiro Aono, EP 1845091 (2007 to Kyorin Pharmaceutical Co., Ltd.).
^Hiroyuki Miyachi, Kei Okazaki, Hiromi Kiyota, Mitsuru Segawa, U.S. patent 5,932,607 (1999 to Kyorin Pharmaceutical Co., Ltd.).
^Cai Hongfei, et al. CN 103772286 (2014 to Jiangxi Qingfeng Pharmaceutical Co Ltd).
^Jinchun Tang & Sunan Wang, CN1 02030682A (2010 to Changzhou Kangpu Pharmaceutical Co Ltd).
^Reid, Wm. B., Hunter, J. H. (October 1948). "Preparation of Diphenylacetonitrile". Journal of the American Chemical Society. 70 (10): 3515–3515. doi:10.1021/ja01190a509.
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