Triethylamine → HCID 67082857, compound

Participants

Reaction Steps

3-[4-(1-Methyl-pentyl)-phenyl]-N-quinolin-3-yl-propionamide. 4-(1-Methyl-pentyl)-benzoic acid from step B (0.114 g, 0.55 mmol) was dissolved in 5 mL DMF with stirring. To this was added Et3N (0.10 mL, 0.72 mmol), 3-aminoquinoline (0.082 g, 0.57 mmol) and lastly HBTU (0.224 g, 0.59 mmol). The reaction was allowed to stir overnight then poured into 25 mL EtOAc and washed with saturated NaHCO3 solution (25 mL) then brine (25 mL). The organics were dried over Na2SO4, filtered, evaporated in vacuo and the residue chromatographed over silica gel eluting with 0% to 40% EtOAc in hexanes. Evaporation of the proper fractions yielded the title product (0.120 g, 0.36 mmol). 1H NMR (DMSO-d6): 8.93 (d, 1H), 8.86 (d, 1H), 8.09 (m, 2H), 7.88 (m, 3H), 7.67 (dt, 1H), 7.57 (t, 1H), 7.35 (d, 2H), 2.79 (h, 1H), 1.61 (q, 2H), 1.37-1.04 (m, 7H), 0.87 (t, 3H); MS: m/z 333.4 (MH+).

Provenance & Evidence