Ethylamine → HCID 57344515, compound

Participants

Reaction Steps

To a round bottomed flask was added tert-butyl 2-((4S)-6-(4-chlorophenyl)-1-methyl-4H-benzo[c]isoxazolo[4,3-e]azepin-4-yl)acetate (0.059 g, 0.140 mmol), CH2Cl2 (2 mL), and TFA (0.400 mL, 5.19 mmol). The reaction was stirred at room temperature for 2 h before concentrating. The crude residue was dried for 30 min before addition of DMF (2 mL), ethylamine (0.098 mL, 0.195 mmol, 2M in THF), HATU (0.080 g, 0.209 mmol), and Hunig's Base (0.073 mL, 0.419 mmol). The reaction was stirred at room temperature for 1 h before diluting with water and extracting with EtOAc. The combined organics were washed with brine, dried over Na2SO4, filtered, and concentrated. The crude residue was purified via Biotage (EtOAc/hex) to afford 2-((4S)-6-(4-chlorophenyl)-1-methyl-4H-benzo[c]isoxazolo[4,3-e]azepin-4-yl)-N-ethylacetamide (0.022 g, 0.056 mmol). 1H NMR (500 MHz, Acetone-d6) δ 7.76-7.72 (m, 1H), 7.71-7.66 (m, 1H), 7.49-7.42 (m, 3H), 7.41-7.36 (m, 3H), 7.32 (br. s, 1H), 4.62 (dd, J=5.4, 8.3 Hz, 1H), 3.35-3.21 (m, 2H), 3.20-3.09 (m, 2H), 2.67 (s, 3H), 1.14 (t, J=7.3 Hz, 3H); LC/MS m/z 394.

Provenance & Evidence