Triethylamine → HCID 59176612, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-((1-(2-(aminomethyl)phenyl)-1H-1,2,3-triazol-4-yl)methyl)-N-methyl-5,6,7,8-tetrahydroquinolin-8-amine tetrahydrochloride, AD, (0.20 g, 0.43 mmol) in methanol (2 mL) was added 2-pyridine carboxaldehyde (0.04 mL, 0.43 mmol) and triethylamine (0.18 mL, 1.30 mmol). The reaction mixture was heated to 60° C. and stirred for 18 h. The reaction mixture was then cooled to room temperature and NaBH4 (0.05 g, 1.30 mmol) was added. The reaction stirred 1 h at room temperature. The reaction mixture was poured into brine (10 mL) and was extracted with ethyl acetate (2×10 mL). The combined organic phases were dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by chromatography on basic alumina (0-5% methanol/dichloromethane) yielding AG. ESI+ MS: m/z (rel intensity) 440 (100, M+H).

Provenance & Evidence