Reference of 1003-21-0, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 1003-21-0 as follows.
iPrMgCl (2.06 M in THF, 0.72 mL, 1.48 mmol) was added dropwise at 0 C. over 1.5 minutes to a solution of 5-bromo-1,2-dimethyl-1H-imidazole (0.257 g, 1.60 mmol) in THF (4 mL; dried over 3 A molecular sieves) under argon. After stirring for 17 minutes, a solution of tert-butyl 4-(4-chloro-2-methoxy-3-((tetrahydro-2H-pyran-4-yl)methyl)quinoline-6-carbonyl)piperidine-1-carboxylate (0.452 g, 0.899 mmol, Intermediate 5) and LaCl3-2LiCl (0.5 M in THF, 1.98 mL, 0.988 mmol) in THF (2 mL) was added dropwise over 2 minutes to the Grignard reagent at 0 C., and after 30 minutes the reaction was quenched with 5 M aqueous NH4Cl (1 mL). The aqueous layer was extracted with DCM (1*5 mL), and the combined organic layers were dried (Na2SO4), filtered, and concentrated. The residue was purified by FCC (0-10% MeOH in DCM) to afford the title compound as a white foam. 1H NMR (400 MHz, CDCl3) delta 8.10 (br. s., 1H), 7.74 (d, J=8.59 Hz, 1H), 7.34-7.41 (m, 1H), 7.29 (s, 1H), 7.18 (s, 1H), 4.25 (br. s., 1H), 4.07 (s, 3H), 3.91-3.98 (m, 2H), 3.28-3.38 (m, 2H), 3.23 (s, 3H), 2.90 (d, J=7.07 Hz, 2H), 2.55-2.85 (m, 2H), 2.31-2.42 (m, 1H), 2.18-2.26 (m, 1H), 1.91-2.04 (m, 1H), 1.66 (br. s., 3H), 1.49-1.59 (m, 3H), 1.41 (s, 9H), 1.29-1.38 (m, 1H), 1.13-1.23 (m, 2H); MS m/e 584.8 [M+H]+.
According to the analysis of related databases, 1003-21-0, the application of this compound in the production field has become more and more popular.
Reference:
Patent; JOHNSON & JOHNSON; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem