{"id":5986,"date":"2021-08-23T03:09:08","date_gmt":"2021-08-22T19:09:08","guid":{"rendered":"https:\/\/www.pyrazoles-derivatives.com\/?p=5986"},"modified":"2021-08-23T03:09:08","modified_gmt":"2021-08-22T19:09:08","slug":"a-new-synthetic-route-of-578008-32-9","status":"publish","type":"post","link":"https:\/\/www.pyrazoles-derivatives.com\/?p=5986","title":{"rendered":"A new synthetic route of 578008-32-9"},"content":{"rendered":"

Application of 578008-32-9<\/a>, A common heterocyclic compound, 578008-32-9, name is tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate, molecular formula is C9H15N3O2, 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.<\/p>\n

Step D: To 4-chloro-2-[difluoro-(5-fluoro-pyridin-2-yl)-methyl]-8-bromo-quinazoline (0.19 g, 0.49 mmol) in DMA (1.0 mL) were added 3-amino-5-methyl-pyrazole-1-carboxylic acid tert-butyl ester (0.30 g, 1.53 mmol) and HOAc (0.065 mL, 1.1 mmol) and the mixture was heated to 100 C. for 5 h. The mixture was allowed to cool to rt and purified by reverse phase HPLC (ammonium acetate modifier). Fraction 1 containing pure product was treated with saturated aq NaHCO3 (2-4 mL) and concentrated under reduced pressure. The aqueous residue was extracted with DCM (3\u00d730 mL) and the combined extracts were washed with sat aqueous NaHCO3 (10 mL) and brine (10 mL), dried over MgSO4, filtered, and concentrated to dryness under reduced pressure to afford 8-bromo-2-(difluoro(5-fluoropyridin-2-yl)methyl)-N-(5-methyl-1H-pyrazol-3-yl)quinazolin-4-amine (48 mg, 20%) as a white solid. 1H NMR (300 MHz, DMSO-d6) delta 12.22 (br s, 1H), 10.87 (br s, 1H), 8.57-8.81 (m, 2H), 8.24 (d, J=7.5 Hz, 1H), 8.02 (d, J=5.3 Hz, 2H), 7.54 (t, J=7.9 Hz, 1H), 5.95 (s, 1H), 2.17 (s, 3H); LC-MS (ESI) m\/z 449\/451 (M+H+).<\/p>\n

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.<\/p>\n

Reference:
Patent; Hadd, Michael J.; Holladay, Mark W.; Rowbottom, Martin; US2012\/53174; (2012); A1;<\/a>,
Pyrazole – Wikipedia<\/a>,
Pyrazoles – an overview | ScienceDirect Topics<\/p>\n","protected":false},"excerpt":{"rendered":"

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. 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