Diisopropylethylamine → HCID 59451645, compound

Participants

Reaction Steps

3-{[5-(Aminomethyl)-2-chlorophenyl]oxy}-5-chlorobenzonitrile (0.15 g, 0.51 mmol), 2-methyl-4-(methyloxy)benzoic acid (0.6 g, 0.25 mmol), HATU (0.21 g, 0.56 mmol) and DIPEA (0.11 mL, 0.60 mmol) were dissolved in acetonitrile (3 mL) and DMF (1 mL) then stirred overnight. EtOAc (25 mL) and saturated NaHCO3 (10 mL) were added. The layers were separated and the aqueous layer was extracted with EtOAc (2×10 mL). The organic extracts were combined, dried over Na2SO4, filtered and evaporated. Purification was accomplished by Reverse-Phase HPLC (water/acetonitrile with 0.1% TFA) to afford the title compound (0.05 g, 19%) as a white solid. 1H NMR (400 MHz, DMSO-d5): δ ppm 8.63 (s, 1H), 7.82 (d, 1H), 7.59 (d, 1H), 7.46 (dd, 1H), 7.39 (d, 1H), 7.26 (t, 2H), 7.16 (d, 1H), 6.73-6.78 (m, 2H), 4.38 (d, 2H), 3.73 (s, 3H), 2.25 (s, 3H). MS: m/z 441.0 (M+1).

Provenance & Evidence