These common heterocyclic compound, 16066-84-5, name is tert-Butyl methylcarbamate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 16066-84-5
To a stirred suspension of 6-iodo-3 -((8-methoxy-2-(6-methoxypyridin-3 -yl)-2,3dihydrobenzo[b] [1 ,4]dioxin-6-yl)methyl)-3H-imidazo[4, 5-b]pyridine (0.20 g, 0.38 mmol, Example 1-52-9) in 1,4-dioxane (5 mL) was added tert-butyl-N-methylcarbamate (0.10 g,0.75 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.018 g, 0.019 mmol), 4,5- bi s(diphenylphosphino)-9, 9-dimethylxanthene (0.044 g, 0.075 mmol) and cesium carbonate (0.18 g, 0.57 mmol). The mixture was degassed under vacuum/backfilled with nitrogen (x3). The mixture was then heated to 115 C. After 18 h, the mixture was allowed to cool to room temperature and was concentrated. Chromatographic purification of the crude product(Biotage, 12 g silica gel column, ethyl acetate/heptane elute) provided semi-pure material. This material was dissolved in dichloromethane (10 mL) and was treated with trifluoroacetic acid (6 mL). The mixture was allowed to stir at room temperature. After 15 mm, the mixture was concentrated. The residue was dissolved in methanol and was neutralized by the addition of solid potassium carbonate. The mixture was filtered and concentrated.Chromatographic purification of the crude product (Biotage, 12 g silica gel column, 0-8% methanol/ethyl acetate elute) provided 0.020 g (12%) of 3-((8-methoxy-2-(6- methoxypyridin-3 -yl)-2,3 -dihydrobenzo[b] [1 ,4]dioxin-6-yl)methyl)-N-methyl-3H- imidazo[4,5-b]pyridin-6-amine as a light yellow solid: ?H NIVIR (400 IVIFIz, CDC13) 8.22 – 8.18 (m, 1H), 7.95 (d, J= 2.5 Hz, 1H), 7.92 (s, 1H), 7.61 (dd, J= 8.6, 2.5 Hz, 1H), 7.28 (d, J= 2.5 Hz, 1H), 6.77 (dd, J= 8.5, 0.7 Hz, 1H), 6.54 – 6.48 (m, 2H), 5.30 (s, 2H), 5.09 (dd, J8.4, 2.5 Hz, 1H), 4.29 (dd, J= 11.6, 2.5 Hz, 1H), 4.06 (dd, J= 11.6, 8.4 Hz, 1H), 3.93 (s, 3H), 3.79 (s, 3H), 2.91 (s, 3H) ppm; (M+1) = 434.
Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 16066-84-5.
Reference:
Patent; GENZYME CORPORATION; KANE, John, L., Jr.; BARBERIS, Claude; CZEKAJ, Mark; ERDMAN, Paul; GIESE, Barret; KOTHE, Michael; LE, Tieu-binh; LIU, Jinyu; MA, Liang; METZ, Markus; PATEL, Vinod; SCHOLTE, Andrew; SHUM, Patrick; WEI, Limli; (408 pag.)WO2017/15267; (2017); A1;,
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