Triethylamine → HCID 46847186, compound

Participants

Reaction Steps

2-(Trimethylsilyl)ethyl 4-(4-phenylpiperazin-1-yl)isoquinoline-6-carboxylate (2.37 g, 5.47 mmol) produced in Example 3 (3d) was dissolved in tetrahydrofuran (27 mL), to which a 1.0M n-tetrabutylammonium fluoride/tetrahydrofuran solution (16.4 mL, 16.4 mmol) was then added, followed by stirring at room temperature for 1.5 hours. The solvent was distilled off under reduced pressure. The residue thus obtained was dissolved in N,N-dimethylformamide (47 mL) under a nitrogen atmosphere, to which ammonium chloride (2.92 g, 54.7 mol), triethylamine (9.14 mL, 65.6 mmol), 1-hydroxybenzotriazole (251 mg, 1.64 mmol), and N-[3-dimethylaminopropyl]-N′-ethylcarbodiimide hydrochloride (5.24 g, 27.3 mmol) were added, followed by stirring at room temperature for 13 hours. The resulting reaction liquid was filtered and the solvent was distilled off under reduced pressure. The residue thus obtained was purified by basic silica gel column chromatography (hexane:ethyl acetate, 50:50-0:100, V/V) and recrystallized from a mixed solvent of ethanol-dichloromethane to give the desired title compound (1.13 g, yield 62%).

Provenance & Evidence