Piperidine → HCID 11429825, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-amino-5-chlorobenzophenone (230 mg, 1.00 mmol), 5-bromo-3-pyridineacetic acid (215 mg, 1.00 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDCI) (230 mg; 1.20 mmol) in DCM (2.5 mL) was stirred overnight at room temperature. Toluene (2.5 mL) and piperidine (0.2 mL) were then added and the resulting solution was heated to approximately 100° C., allowing the DCM to evaporate from the reaction mixture. After 2 h, the reaction was allowed to cool and stirring was continued at room temperature overnight. The precipitate that formed was filtered and washed with toluene. This crude product was dissolved in chloroform and extracted with water (4×), dried over potassium carbonate (K2CO3) and concentrated to afford the pure quinolinone product (285 mg, 69%). 1H NMR (300 MHz, DMSO-d6) δ 12.4 (br.s, 1H), 8.45 (d, 1H, J=3.0 Hz), 8.21 (d, 1H, J=1.3 Hz), 7.86 (t, 1H, J=1.5 Hz), 7.64 (dd, 1H, J=8.9, 2.3 Hz, 1H), 7.46 (d, 1H, J=8.6 Hz), 7.44-7.31 (m, 3H), 7.28-7.21 (m, 2H), 6.94 (d, 1H, J=2.0 Hz). MS: 413.0 (M+H).

Provenance & Evidence