Anthranilamide → HCID 22200422, compound

Participants

Reaction Steps

To a mixture of [4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-acetic acid (1.10 g, 3.5 mmol), HATU (1.33 g, 3.5 mmol) and DIEA (1.22 mL, 7 mmol) in dichloromethane (40 mL) was added anthranilamide (714 mg, 5.25 mmol). The reaction was stirred at room temperature for 1 hour and then the reaction mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (50-100% ethyl acetate-hexanes) to yield the pure product. (1.18 g, 78%). 1H NMR (400 MHz, CDCl3) δ 11.82 (s, 1H), 8.66 (d, J=8.0 Hz, 1H), 7.77 (d, J=7.0 Hz, 2H), 7.51 (m, 2H), 7.11 (t, J=7.6 Hz, 1H), 7.05 (d, J=7.1 Hz, 2H), 6.10 (br s, 1H), 5.51 (br s, 1H), 3.92 (s, 3H), 3.24 (m, 6H), 2.76 (t, J=4.7 Hz, 4H); HPLC ret. time 2.46 min, 10-99% CH3CN, 5 min run; ESI-MS m/z 433.1 (M+1)+.

Provenance & Evidence