With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14161-11-6,3,4,5-Trichloropyridazine,as a common compound, the synthetic route is as follows.
A mixture of 4-(2-(difluoromethoxy)-3,6- difluorophenyl)piperidine (0.57 g, 2.165 mmol), 20% aqueous potassium carbonate (2.72 ml, 4.33 mmol) and 3,4,5-trichloropyridazine (0.397 g, 2.165 mmol) in dioxane (10 ml) was stirred at 90C for 2h. Hydrazine hydrate (0.799 g, 15.96 mmol) was added and the reaction mixture was stirred at 90 C for 16 h. The mixture was concentrated and the residue was diluted with ethyl acetate and saturated aqueous sodium bicarbonate. The aqueous layer was extracted with ethyl acetate (4x 10 ml). The combined organic layers were washed with additional saturated aqueous sodium bicarbonate, and was used for next step. An aliquot was purified by Prep. HPLC on a Phenomenex-Luna 30 x 100mm S10 Axia column, using 20-80% methanol/water containing 0.1% TFA to give 4-chloro-5-(4-(2-(difluoromethoxy)-3,5- difluorophenyl)piperidin-l-yl)-3-hydrazinylpyridazine for characterization. XH NMR (400MHz, METHANOL-d4) delta 8.39 (s, 1H), 7.23 – 7.14 (m, 1H), 7.12 – 7.05 (m, 1H), 6.86 (t, j=74.0 Hz, 1H), 3.89 – 3.79 (m, 2H), 3.44 – 3.34 (m, 1H), 3.05 (t, j=12.4 Hz, 2H), 2.42 – 2.24 (m, 2H), 1.87 – 1.73 (m, 2H). LCMS: M+l = 405.9.
14161-11-6, The synthetic route of 14161-11-6 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; MATTSON, Ronald J.; MENG, Zhaoxing; GUERNON, Leatte R.; WO2013/192306; (2013); A1;,
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