Triethylamine → HCID 178491178, compound

Participants

Reaction Steps

To a 50 ml round bottom flask equipped with a magnetic stir bar were added (4-methoxyphenyl)(2-methyl-1H-imidazol-4-yl)methanaminium chloride (0.350 g, 1.206 mmol), 4-cyclopropylphenylacetic acid (0.213 mg, 1.206 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.231 g, 1.206 mmol), 1-hydroxy-7-azabenzotriazole (0.164 mg, 1.206 mmol) and triethylamine (0.336 ml, 2.412 mmol) into 10.0 ml of CH2Cl2. The resulting solution was stirred at room temperature for 16 hours. The reaction mixture was diluted with water and the two layers were separated. The aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuum. Purification by flash chromatography (SiO2, 0-10% methanol in CH2Cl2, gradient) gave the title compound as a white solid (0.260 g, 57%). 1H NMR (CDCl3, 400 MHz) δ 7.151 (m, 4H), 7.021 (d, J=8.24 Hz, 2H), 7.820 (d, J=8.60 Hz, 2H), 6.459 (s, 1H), 6.459 (br s, 1H), 5.989 (d, J=7.32 Hz, 1H), 3.778 (s, 3H), 3.552 (s, 2H), 2.355 (s, 3H), 1.870 (m, 1H), 0.950 (m, 2H), 0.669 (m, 2H). ES-MS [M+1]+: 376.3.

Provenance & Evidence