548762-66-9, (2S,5R)-tert-Butyl 2,5-dimethylpiperazine-1-carboxylate is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,548762-66-9
A solution of 6-chloro-1-(3,5-diisopropylpyridazin-4-yl)-7-(2-fluorophenyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (0.439 g, 0.967 mmol, Intermediate 212), phosphoryl trichloride (0.108 mL, 1.16 mmol), and DIPEA (0.168 mL, 0.967 mmol) in acetonitrile (5 mL) was stirred under an air condensor and drying tube at 80 C. for 30 min. The reaction mixture was cooled to RT, and tert-butyl (2S,5R)-2,5-dimethylpiperazine-1-carboxylate (0.207 g, 0.967 mmol; eNovation Chemicals LLC, Bridgewater, N.J.) was added; the solution was stirred a RT for 30 min. The reaction mixture was diluted with EtOAc (200 mL), added to a separatory funnel, and washed with saturated, aqueous sodium bicarbonate (2*100 mL); the organic layer was separated, dried over anhydrous Na2SO4, and concentrated in vacuo. The crude product was adsorbed onto silica and was purified via automated flash chromatography (silica gel. 0-100% EtOAc/heptane) to give tert-butyl (2S,5R)-4-(6-chloro-1-(3,5-diisopropylpyridazin-4-yl)-7-(2-fluorophenyl)-2-oxo-1,2-dihydropyrido[2,3-d]pyrimidin-4-yl)-2,5-dimethylpiperazine-1-carboxylate (258 mg, 0.397 mmol, 41% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) delta 9.11 (d, J=2.3 Hz, 1H) 8.13 (d, J=1.9 Hz, 1H) 7.38-7.47 (m, 1H) 7.05-7.18 (m, 3H) 4.16-5.08 (m, 3H) 3.76-4.08 (m, 2H) 3.45-3.65 (m, 1H) 2.70-2.82 (m, 1H) 2.58-2.70 (m, 1H) 1.52 (s, 9H) 1.24-1.37 (m, 12H) 1.17 (dd, J=9.1, 6.8 Hz, 3H) 1.04 (dd, J=6.7, 4.7 Hz, 3H). 19F NMR (377 MHz, CDCl3) delta -113.34–113.24 (m, 1F). MS (ESI, +ve) m/z: 650.2 (M+1)+.
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Reference£º
Patent; Amgen Inc.; ALLEN, John Gordon; LANMAN, Brian Alan; CHEN, Jian; REED, Anthony B.; CEE, Victor J.; LIU, Longbin; LOPEZ, Patricia; WURZ, Ryan Paul; NGUYEN, Thomas T.; Booker, Shon; ALLEN, Jennifer Rebecca; CHU-MOYER, Margaret; AMEGADZIE, Albert; CHEN, Ning; GOODMAN, Clifford; LOW, Jonathan D.; MA, Vu Van; MINATTI, Ana Elena; NISHIMURA, Nobuko; PICKRELL, Alexander J.; WANG, Hui-Ling; SHIN, Youngsook; SIEGMUND, Aaron C.; YANG, Kevin C.; TAMAYO, Nuria A.; WALTON, Mary; XUE, Qiufen; US2019/374542; (2019); A1;,
Piperazine – Wikipedia
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