With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4677-20-7,4-(2-Bromoethyl)tetrahydropyran,as a common compound, the synthetic route is as follows.
(rac)-Ethyl 4-chloro-3-ethyl-7-{3-[(6-fluoronaphthalen-1 -yl)oxy]propyl}-2-methyl- 10,11 ,12,13,14,15-hexahydro-2H-pyrazolo[3′,4′:8,9][1 ,6]diazacycloundecino[10,11 ,1 -hi]indole- 8-carboxylate (see Intermediate 115, 50.0 mg, 81.0 pmol), 4-(2-bromoethyl)oxane (17.2 mg, 89.1 pmol) and cesiumcarbonate (132 mg, 405 pmol) were dissolved in 410 mI_ DMF and the reaction mixture was stirred at 600 in a sealed ve ssel under nitrogen atmosphere. The reaction mixture was diluted with water and dichloromethane, stirred for a few minutes, filtered through a silicone coated filter and concentrated under reduced pressure. The crude product was purified by HPLC chromatography under basic conditions to provide the target compound in 99% purity: 23 mg. LC-MS (Methode 2): Rt = 1.85 min; MS (ESIpos): m/z = 730 [M+H]+ 1 H-NMR (400MHz, DMSO-d6): d [ppm]= 0.55 – 0.74 (m, 1 H), 0.75 – 0.96 (m, 7H), 1.00 – 1.13 (m, 3H), 1.13 – 1.32 (m, 7H), 1.83 – 1.93 (m, 2H), 2.03 – 2.27 (m, 4H), 2.35 – 2.47 (m, 2H), 2.88 (td, 1 H), 2.97 (d, 1 H), 3.19 – 3.31 (m, 2H), 3.50 (br d, 1 H), 3.59 (br dd, 1 H), 3.72 – 3.93 (m, 5H), 4.04 – 4.16 (m, 1 H), 4.17 – 4.39 (m, 4H), 6.90 (dd, 1 H), 7.24 (d, 1 H), 7.37 – 7.50 (m, 3H), 7.67 (dd, 1 H), 7.75 (d, 1 H), 8.30 (dd, 1 H). As side product of the reaction to Intermediate 202the target compound was isolated in 98% purity: 12 mg. LC-MS (Methode 2): Rt = 1.77 min; MS (ESIpos): m/z = 774 [M+H]+ 1 H-NMR (400MHz, DMSO-d6): d [ppm]= 0.83 (t, 3H), 0.91 (br d, 2H), 0.98 – 1.17 (m, 4H), 1.18 – 1.31 (m, 5H), 1.32 – 1.56 (m, 5H), 2.13 – 2.31 (m, 4H), 3.08 – 3.31 (m, 4H), 3.75 (br dd, 2H), 3.80 – 3.98 (m, 6H), 3.99 – 4.35 (m, 5H), 4.36 – 4.53 (m, 2H), 6.86 (dd, 1 H), 7.25 (br d, 1 H), 7.34 – 7.49 (m, 3H), 7.66 (dd, 1 H), 7.80 (d, 1 H), 8.24 (dd, 1 H).
4677-20-7, As the paragraph descriping shows that 4677-20-7 is playing an increasingly important role.
Reference£º
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; THE BROAD INSTITUTE, INC.; THEDE, Kai; MENGEL, Anne; CHRIST, Clara; KUHNKE, Joachim; JOHANNES, Sarah, Anna, Liesa; BUCHGRABER, Philipp; KLAR, Ulrich; SACK, Ulrike; KAULFUSS, Stefan; FERNANDEZ-MONTALVAN, Amaury, Ernesto; WERBECK, Nicolas; MOeNNING, Ursula; NOWAK-REPPEL, Katrin; LEMKE, Chris; SERRANO-WU, Michael, H.; MCKINNEY, David; FITZGERALD, Mark; NASVESCHUK, Christopher; LAZARSKI, Kiel; FERRARA, Steven, James; FURST, Laura; WEI, Guo; MCCARREN, Patrick, Ryan; HARVEY, Rebecca, Ann; PAYNE, Daniel; PESNOT, Thomas; WILSON, Craig; (683 pag.)WO2019/96905; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics