149353-75-3, 4-(1-(tert-Butoxycarbonyl)piperidin-4-yl)benzoic acid is a piperidines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
Production Example 1-8 tert-Butyl 4-(4-((4-((6-methoxy-1-(methylcarbamoyl)-1H-indol-5-yl)oxy)pyridin-2-yl)carbamoyl)phenyl)piperidine-1-carboxylate Benzotriazole (2.32 g, 19.5 mmol) was dissolved in dichloromethane (100 mL), thionyl chloride (1.4 mL, 19.2 mmol) was added under nitrogen atmosphere at room temperature, and the mixture was stirred for 5 minutes. 4-(1-(tert-Butoxycarbonyl)piperidin-4-yl)benzoic acid described in Production Example 1-12 (5.4 g, 17.7 mmol) was added to the reaction mixture at mom temperature, and the mixture was stirred for 25 minutes. The reaction mixture was filtered through a glass filter entirely covered with anhydrous sodium sulfate and then washed with dichloromethane, then the filtrate was added to a mixture of 5-((2-aminopyridin-4-yl)oxy)-6-methoxy-N-methyl-1H-indole-1-carboxamide described in Production Example 1-6 (2.5 g, 8.01 mmol), triethylamine (11 mL, 79.4 mmol), and 4-dimethylaminopyridine (101 mg, 0.827 mmol) in tetrahydrofuran (80 mL) at 0 C. The resultant was stirred at mom temperature for 5 hours and then the reaction mixture was concentrated under vacuum. Water and ethyl acetate were added to the residue for partition, and the organic layer was washed with a saturated saline solution, and then dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under vacuum, the residue was dissolved in tetrahydrofuran, an excessive quantity of 9.8 M methylamine methanol solution was added at room temperature, and the mixture was stirred for 50 minutes. The reaction mixture was concentrated under vacuum, the residue was dissolved in dichloromethane, and the resultant was purified with NH silica gel column chromatography (n-heptane:ethyl acetate=1:1-1:3-0:1). The target fraction was concentrated under vacuum and the precipitate was collected by filteration and washed with diethyl ether and ethyl acetate to obtain the title compound (3.15 g, 66%). The filtrate was combined with the mixture fraction and the resultant was concentrated under vacuum and dissolved in dichloromethane, and the resultant was purified with NH silica gel column chromatography (n-heptane:ethyl acetate=1:1-1:3-0:1). The target fraction was concentrated under vacuum and the precipitate was collected by filteration and washed with diethyl ether and ethyl acetate to obtain the title compound (264 mg, 5.5%). 1H-NMR Spectrum (CDCl3) delta (ppm): 1.48 (9H, s), 1.55-1.69 (2H, m), 1.77-1.87 (2H, m), 2.64-2.89 (3H, m), 3.02-3.07 (3H, m), 3.86 (3H, s), 4.26 (2H, brs), 5.62 (1H, brs), 6.50-6.55 (1H, m), 6.61 (1H, dd, J=5.9, 2.2 Hz), 7.22 (1H, d, J=3.7 Hz), 7.27-7.33 (3H, m), 7.80 (2H, d, J=8.4 Hz), 7.90 (1H, d, J=2.2 Hz), 8.04 (1H, s), 8.09 (1H, d, J=5.9 Hz), 8.54 (1H, brs)., 149353-75-3
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Reference£º
Patent; Eisai R&D Management Co., Ltd.; Funasaka, Setsuo; Okada, Toshimi; Tanaka, Keigo; Nagao, Satoshi; Ohashi, Isao; Yamane, Yoshinobu; Nakatani, Yusuke; Karoji, Yuki; US2014/235614; (2014); A1;,
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