Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 24134-09-6, name is 5-Bromo-1,2-dimethyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 24134-09-6
A 2.5 M solution of n-butyllithium in hexanes (0.260 mL, 0.650 mmol) was added dropwise to a dry ice-acetone cooled solution of 5-bromo-1,2-dimethyl-1H-imidazole (120 mg, 0.686 mmol) in tetrahydrofuran (2 mL). After 30 seconds, a solution of (4-chloro-2-methoxy-3-((4-(2,2,2-trifluoroethyl)piperazin-1-yl)methyl)quinolin-6-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanone (157 mg, 0.325 mmol, Intermediate 17: step b) in tetrahydrofuran (1 mL) was added dropwise by syringe. After 2 minutes, the flask was removed from the cooling bath. After 3 minutes, the flask was placed into an ice-water bath. After 45 minutes, water (20 mL) and ethyl acetate (50 mL) were added sequentially. The layers were separated. The organic layer was dried with sodium sulfate and the dried solution was filtered. Celite (7 g) was added to the filtrate and the mixture was concentrated in vacuo. The dry solid was loaded onto a silica gel column for flash-column chromatography. Elution with dichloromethane initially, grading to 10% methanol-dichloromethane provided impure title compound. Further purification by RP-HPLC eluting with 5% acetonitrile-water containing 0.2% TFA and partitioning of the combined fractions between dichloromethane-saturated aqueous sodium bicarbonate solution provided the title compound as a white solid. 1H NMR (500 MHz, CDCl3) delta ppm 8.20 (d, J=2.2 Hz, 1H), 7.72 (d, J=8.7 Hz, 1H), 7.41-7.34 (m, 1H), 7.12 (s, 1H), 6.05 (s, 1H), 5.89 (s, 1H), 4.09 (s, 3H), 3.91 (s, 3H), 3.88-3.80 (m, 2H), 3.37 (s, 3H), 2.99-2.87 (m, 2H), 2.65 (s, 8H), 2.24 (s, 3H); MS (ESI): mass calcd. for C26H30ClF3N8O2, 578.2. m/z found, 579.1 [M+H]+. (4-Chloro-2-methoxy-3-((4-(2,2,2-trifluoroethyl)piperazin-1-yl)methyl)quinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanol was purified by chiral SFC (Chiralpak AD-H, 5 mum, 250 mm¡Á30 mm, mobile phase: 85% CO2, 15% isopropanol containing 0.2% isopropylamine) to provide two enantiomers. The first eluting enantiomer was Example 17b: 1H NMR (500 MHz, CDCl3) delta ppm 8.17 (d, J=2.1 Hz, 1H), 7.75 (d, J=8.7 Hz, 1H), 7.40-7.35 (m, 1H), 7.18 (s, 1H), 6.13 (s, 1H), 4.54 (s, 1H), 4.09 (s, 3H), 3.92 (s, 3H), 3.85 (s, 2H), 3.40 (s, 3H), 2.98-2.89 (m, 2H), 2.70-2.62 (m, 8H), 2.33 (s, 3H); MS (ESI): mass calcd. for C26H30ClF3N8O2, 578.2. m/z found, 579.1 [M+H]+ and the second eluting enantiomer was Example 17c: 1H NMR (500 MHz, CDCl3) delta ppm 8.16 (d, J=2.2 Hz, 1H), 7.77 (d, J=8.7 Hz, 1H), 7.41-7.36 (m, 1H), 7.20 (s, 1H), 6.16 (s, 1H), 4.16-4.06 (m, 4H), 3.93 (s, 3H), 3.86 (s, 2H), 3.41 (s, 3H), 2.98-2.88 (m, 2H), 2.71-2.61 (m, 8H), 2.35 (s, 3H); MS (ESI): mass calcd. for C26H30ClF3N8O2, 578.2. m/z found, 579.1 [M+H]+.
Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 24134-09-6.
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;,
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