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. 60166-43-0, name is 1,4-Dimethyl-1H-1,2,3-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 60166-43-0
In a 75 mL pressure vessel equipped with a magnetic stirring bar, was added (5)- 3-bromo-7-chloro-5-((2-fluorophenyl)(tetrahydro-2H-pyran-4-yl)methyl)-5H-pyrrolo[2,3- b:4,5-b’]dipyridine (650 mg, 1.37 mmol), l,4-dimethyl-lH-l,2,3-triazole (199 mg, 2.05 mmol) and NMP (10 mL). Tetramethyl NH4OAC (274 mg, 2.05 mmol) and bis(triphenylphosphine) palladium(II) chloride (67.3 mg, 0.096 mmol) was added. Argon was bubbled into the mixture with sonication for 5 min, then the vessel was capped and placed into a preheated oil bath at 100C. The reaction mixture was stirred overnight. Most of the solvent was removed under a stream of nitrogen while heating for several hours in an oil bath set at 100C. The remaining mixture was taken up in 2 mL of DMF then filtered for purification by preparative HPLC: Column: Waters XBridge CI 8, 19 x 200 mm, 5-muiotatauiota particles; Mobile Phase A: 5:95 methanol: water with lOmM NLUOAc; Mobile Phase B: 95:5 methanol: water with lOmM NHtOAc; Gradient: 10-80% B over 30 min, then a 5-min hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation to give 4.7 mg (0.6%) of the title compound with an average purity by LC/MS analysis was >99%. Two analytical LC/MS injections were used to determine the final purity. Injection 1 conditions: Column: Waters BEH C18, 2.0 x 50 mm, 1.7um particles; Mobile Phase A: 5:95 ACN:water with 10 mM NH4OAc; Mobile Phase B: 95:5 ACN:water with 10 mM NH4OAc; Temperature: 50C; Gradient: 0%B, 0-100% B over 3 min, then a 0.5-min hold at 100% B; Flow: 1 mL/min; Detection: UV at 220 nm. Rt= 1.50 min; LC/MS (M+H) = 552.5. Injection 2 conditions: Column: Waters BEH C18, 2.0 x 50 mm, 1.7-mupiiota particles; Mobile Phase A: 5:95 methanol: water with 10 mM NFL Ac; Mobile Phase B: 95:5 methanol: water with 10 mM NH4OAc; Temperature: 50C; Gradient: 0%B, 0-100% B over 3 min, then a 0.5-min hold at 100% B; Flow: 0.5 mL/min; Detection: UV at 220 nm. Rt= 2.51 min; LC/MS (M+H) = 552.5. NMR (500MHz, DMSO-c e) delta 8.81 (d, J=8.1 Hz, 1H), 8.68 (s, 1H), 8.46 (br. s., 1H), 8.20 (br. s., 1H), 7.71 (d, J=8.1 Hz, 1H), 7.34 (d, J=5.5 Hz, 1H), 7.29 (d, J=7.7 Hz, 1H), 7.17 – 7.04 (m, 1H), 6.36 (br. s., 1H), 4.34 (br. s., 3H), 4.00 (br. s., 3H), 3.93 – 3.83 (m, 1H), 3.72 (d, J=9.5 Hz, 1H), 3.47 – 3.38 (m, 4H), 3.27 – 3.15 (m, 1H), 2.29 (br. s., 3H), 1.72 (d, J=11.7 Hz, 1H), 1.58 – 1.42 (m, 1H), 1.33 (d, J=12.1 Hz, 1H), 0.98 (d, J=13.2 Hz, 1H). LC/MS (M+H) = 552.5; HPLC conditions: Rt= 2.57 min (Phenomenex LUNA C18 2 x 50 mm (4 min grad) eluting with 5-95% aq ACN containing lOmM NH4OAC, 0.8 mL/min, monitoring at 254 nm); Temperature: 40C).
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Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; VACCARO, Wayne; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; DELUCCA, George V.; DESKUS, Jeffrey A.; HAN, Wen-Ching; KUMI, Godwin Kwame; SCHMITZ, William D.; STARRETT, John E., JR.; HILL, Matthew D.; HUANG, Hong; (563 pag.)WO2016/183118; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics