New discoveries in chemical research and development in 2021. Chemo-enzymatic cascade processes are invaluable due to their ability to rapidly construct high-value products from available feedstock chemicals in a one-pot relay manner. 202931-88-2, name is 1-Methyl-1H-1,2,3-triazole-5-carbaldehyde belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C4H5N3O
A solution of n-butyllithium in hexanes (1.6 M, 0.71 mE, 1.1 mmol) was added dropwise to a stirring solution of 3-(4-(i R-pyrazol- 1 -yl)benzyl)-6-bromo-4-chloro-2-meth- oxyquinoline (490 mg, 1.1 mmol, Intermediate 4: step d) in tetrahydrofuran (ii mE) at -78C. Afier 2 minutes, a solution of i-methyl-i R-i ,2,3-triazole-5-carbaldehyde (140 mg, 1.1 mmol, Intermediate 18) in tetrahydrofuran (1 mE) was added dropwise. After 5 minutes, the flask was placed into an ice- water bath. Afier 1 hour, water (10 mE) and ethyl acetate (60 mE) were added. The biphasic mixture was stirred for 10 minutes. Ralf-saturated aqueous sodium chloride solution (50 mE) was added and the layers were separated. The organic layer was dried with sodium sulfate and the dried solution was filtered. Silica gel (4 g) was added to the filtrate and the mixture was concentrated by rotary evaporation to afford a free-flowing powder. The powder was loaded onto a silica gel column for flash column chromatography purification. Elution with 100% hexanes initially, grading to 100% ethyl acetate provided the title compound as a white foamwhich was impure. The foam was suspended in methanol (20 mE) and the suspension was sonicated for 5 minutes. The solids were collected by filtration and rinsed with methanol (5 mE). The collected solids were dried to provide the title compound as a white solid. ?H NMR (600 MHz, DMSO-d5) oeppm 8.42 (d, J=2.5 Hz, 1H), 8.21 (d, J=i.8 Hz, 1H), 7.86 (d, J=8.6 Hz, 1H), 7.75-7.71 (m, 2H), 7.72-7.67 (m, 2H), 7.37- 7.32 (m, 3H), 6.55 (d, J=5.2 Hz, 1H), 6.53-6.49 (m, 1H), 6.22 (d, J=5.2 Hz, 1H), 4.30 (s, 2H), 4.04 (s, 3H), 3.97 (s, 3H); MS (ESI): mass calcd. for C24H2,C1N602, 460.1; mlz found, 461.1 [M+H].
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Reference:
Patent; JANSSEN PHARMACEUTICA NV; 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.; US2015/105372; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics