Triethylamine → HCID 178469090, compound

Participants

Reaction Steps

Anhydrous hydrazine (0.17 mL, 5.3 mmol) was added to a solution of compound 14f (1 g, 2.6 mmol) in 20 mL of CH2Cl2 followed by MeOH (20 mL) at room temperature. The reaction mixture was allowed to stir for 1 d. The resulting white precipitates were filtered off and the solvent was removed in vacuo. The resulting white solids were dissolved in aqueous 1N HCl solution and washed with CH2Cl2. The aqueous layer was basified with excess 1N NaOH solution and then extracted with CH2Cl2. After drying with MgSO4, the solvent was evaporated affording crude amine, which was used in the next step without further purification. To a solution of crude amine in DMF (50 mL) was added 4-(trifluoromethoxy)phenyl isocyanate (1.1 g, 4.3 mmol) followed by triethylamine (0.74 mL, 5.3 mmol) at 0° C. The reaction mixture was stirred overnight. The reaction mixture was poured into water, and the resulting precipitates were collected and washed with water. The crude product was purified by column chromatography to give the titled compound (1.7 g, 85%) as a white solid. 1H NMR (CDCl3): δ 7.98 (d, J=9 Hz, 2H), 7.35 (d, J=9 Hz, 2H), 7.13 (d, J=9 Hz, 2H), 6.87 (d, J=9 Hz, 2H), 6.85 (s, 1H), 5.01 (d, J=8 Hz, 1H), 4.57-4.51 (m, 1H), 4.36 (q, J=7 Hz, 2H), 3.89-3.72 (m, 1H), 2.07-1.52 (m, 8H), 1.39 (t, J=7 Hz, 3H). MS (ESI) m/z: 467.2 (M+H+).

Provenance & Evidence