Downstream synthetic route of 108612-54-0

108612-54-0 tert-Butyl methyl(piperidin-4-yl)carbamate 2756806, apiperidines compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.108612-54-0,tert-Butyl methyl(piperidin-4-yl)carbamate,as a common compound, the synthetic route is as follows.

Step A: Preparation of tert-butyl 1-(4-(2-fluoro-4-(2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamido)phenoxy)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)piperidin-4-yl(methyl)carbamate: A round-bottomed flask was charged with N-(4-(1-(4-methoxybenzyl)-3-iodo-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorophenyl)-2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamide (100 mg, 0.142 mmol, prepared in Example 63, step A), tert-butyl methyl(piperidin-4-yl)carbamate (152 mg, 0.708 mmol), copper(I)iodide (5.39 mg, 0.0283 mmol), (S)-pyrrolidine-2-carboxylic acid (6.52 mg, 0.0566 mmol), K2CO3 (97.8 mg, 0.708 mmol) and DMSO (10 mL). The reaction mixture was stirred at 100° C. overnight. The reaction was cooled to ambient temperature and partitioned between EtOAc and H2O. The phases were separated and the aqueous phase was re-extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated to yield a crude product. The crude product was purified by silica gel chromatography (DCM/7 M NH3 in MeOH from 100/1 to 10/1, v/v) to afford product (98.5 mg, 87.8percent). LRMS (APCI pos): m/e 693 (M-99)., 108612-54-0

108612-54-0 tert-Butyl methyl(piperidin-4-yl)carbamate 2756806, apiperidines compound, is more and more widely used in various fields.

Reference:
Patent; Blake, James F.; Boyd, Steven Armen; De Meese, Jason; Fong, Kin Chiu; Gaudino, John J.; Kaplan, Tomas; Marlow, Allison L.; Seo, Jeongbeob; Thomas, Allen A.; Tian, Hongqi; Cohen, Frederick; Young, Wendy B.; US2007/238726; (2007); A1;,
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