Triethylamine → HCID 68433023, compound

Participants

Reaction Steps

To a solution (3 mL) of 4-[5-(methylsulfanyl)pyridin-2-yl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (89.0 mg) in ethanol-tetrahydrofuran (1:1) were added 5-chloropyridine-2-carbaldehyde (86.5 mg), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (8.2 mg) and triethylamine (17 μL), and the mixture was stirred with heating under reflux for 2 h After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was dried (MgSO4) and concentrated. To a solution of the obtained residue (MS: 433 (M)) in acetic acid (2 mL) was added ammonium acetate (376 mg), and the mixture was stirred at 110° C. for 1 hr. After cooling to room temperature, the mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution. The reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (117 mg, yield 92%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio).

Provenance & Evidence