Triethylamine → HCID 86719475, compound

Participants

Reaction Steps

Into a 50 ml round-bottomed flask containing 20 ml of dichloromethane was added 1-(5-fluoro-2,3-dihydro-benzofuran-2-ylmethyl)-piperazine (100 mg, 0.42 mmol), 2-[(4-[[4-nitro-3-(trifluoromethyl)phenyl]amino]cyclohexyl)oxy]acetic acid (230 mg, 0.63 mmol, 1.5 eq), EDAC.HCl (122 mg, 0.64 mmol, 1.5 eq), HOBt (86 mg, 0.64 mmol, 1.5 eq) and triethylamine (128 mg, 1.26 mmol, 3.0 eq). The solution was stirred at room temperature for 16 hours. The crude contents were diluted with water and then extracted with 3×50 ml of ethyl acetate. The organic fractions were combined, dried over magnesium sulfate, filtered, and then concentrated under vacuum. The crude material was then chromatographed on silica gel using methanol/dichloromethane to elute. The product-containing fractions were then combined and concentrated to provide 150 mg of the amide as a light yellow solid (57%). (ES, m/z): [M+H]+ 581.3; 1H NMR (300 MHz, CDCl3): δ 8.02 (d, J=9 Hz, 1H), 6.75-6.91 (m, 3H), 6.60-6.71 (m, 2H), 5.00 (broad s, 1H), 4.48 (d, J=7.5 Hz, 1H), 3.66 (s, 2H), 3.48-3.80 (broad m, 4H), 3.22-3.50 (broad m, 3H), 2.95 (m, 1H), 2.75-2.90 (m, 1H), 2.50-2.75 (broad m, 4H), 2.16 (d, J=8.7 Hz, 4H), 1.38-1.58 (dd, J=10.5, 22.5 Hz, 2H), 1.22-1.34 (dd, J=−10.9, 22.5 Hz, 2H).

Provenance & Evidence