Synthetic Route of 25676-75-9, 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 25676-75-9 as follows.
Example 831 -Methylethyl [(2S,4/?)-1 -acetyl-2-methyl-6-(1 -methyl-1 H-imidazol-4-yl)-1 ,2,3,4- tetrahydro-4-quinolinyl]carbamate h drochlorideA mixture of 1 -methylethyl [(2S,4R)-1 -acetyl-2-methyl-6-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)-1 ,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation, see Intermediate 52) (150 mg, 0.36 mmol), 4-bromo-1 -methylimidazole (0.43 mmol), tetrakis(triphenylphosphine)palladium(0) (42 mg, 10 mol%) and potassium carbonate (199 mg, 1 .44 mmol) in toluene (2 mL) and ethanol (2 mL) was refluxed for 16 h then cooled to room temperature and concentrated in vacuo. The residue was partitioned between AcOEt (10 mL) and water (10 mL) and the layers were separated. The organic phase was dried over MgS04 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 0 to 6% MeOH in DCM) gave a residue which was treated with 1 M HCI in Et20 (0.5 mL, slight excess). The solvent was evaporated and the residue triturated with Et20 to give 1 -methylethyl [(2S,4R)-1 -acetyl-2-methyl-6-(1 -methyl- 1 /-/-imidazol-4-yl)-1 ,2,3,4-tetrahydro-4-quinolinyl]carbamate hydrochloride (8 mg, 0.02 mmol, 5%) as a colourless solid. LCMS (method G): Retention time 0.56 min, [M+H]+ = 371.1
According to the analysis of related databases, 25676-75-9, the application of this compound in the production field has become more and more popular.
Reference:
Patent; GLAXOSMITHKLINE LLC; DEMONT, Emmanuel, Hubert; GARTON, Neil, Stuart; GOSMINI, Romain, Luc, Marie; HAYHOW, Thomas, George, Christopher; SEAL, Jonathan; WILSON, David, Matthew; WOODROW, Michael, David; WO2011/54841; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem