Quipazine → 2-[(4-[[4-Nitro-3-(trifluoromethyl)phenyl]amino]cyclohexyl)oxy]-1-[4-(quinolin-2-yl)piperazin-1-yl]ethan-1-one

Participants

Reaction Steps

To a solution of 2-(piperazin-1-yl)quinoline (150 mg, 0.70 mmol) in dichloromethane (30 ml) was added 2-[(4-[4-nitro-3-(trifluoromethyl)phenyl]aminocyclohexyl)oxy]acetic acid (300 mg, 0.83 mmol, 1.2 eq), EDAC.HCl (201 mg, 1.05 mmol, 1.5 eq), HOBt (142.6 mg, 1.06 mmol, 1.5 eq) and triethylamine (213 mg, 2.10 mmol, 3 eq). The resulting solution was stirred overnight at room temperature, quenched by the addition of water (50 ml), and then extracted with dichloromethane (3×50 ml). The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and then concentrated under vacuum to give a residue. The crude material was purified by Pre-TLC using 5% methanol in dichloromethane to elute. The product-containing fractions were combined and then concentrated under vacuum to afford 229 mg (580) of 2-[(4-[[4-nitro-3-(trifluoromethyl)phenyl]amino]cyclohexyl)oxy]-1-[4-(quinolin-2-yl)piperazin-1-yl]ethan-1-one as a yellow solid. (ES, m/z): [M+H]+ 558.40; 1H NMR (300 MHz, CDCl3): δ 7.94-8.03 (1, 2H), 7.71 (s, 1H), 7.55-7.65 (1, 2H), 7.28-7.30 (t, J=5.4 Hz, 1H), 6.99 (d, J=9.0 Hz, 1H), 6.84 (d, J=2.4 Hz, 1H), 6.61-6.65 (m, 1H), 4.51 (d, J=7.5 Hz, 1H), 4.27 (s, 2H), 3.74-3.96 (1, 8H), 3.34-3.51 (1, 2H), 2.14-2.17 (1, 4H), 1.50-1.60 (m, 2H), 1.36-1.47 (m, 2H).

Provenance & Evidence