3-[4-(Trifluoromethyl)phenyl]prop-2-enoic acid → Rac-n-{2-[methyl-(1-methyl-pyrrolidin-3-ylmethyl)-amino]-benzooxazol-5-yl}-3-(4-trifluoromethyl-phenyl)-acrylamide

Participants

Reaction Steps

Combine rac-N2-methyl-N2-(1-methyl-pyrrolidin-3-ylmethyl)-benzooxazole-2,5-diamine (0.040 g, 0.154 mmol), 3-(4-trifluoromethyl-phenyl)-acrylic acid (0.050 g, 0.230 mmol), HATU (0.058 g, 0.154 mmol), polystyrene-bound diisopropylamine (0.385 g, loading: 2.0 to 3.5 mmol/g), and CH2Cl2 (20 mL). Shake the mixture overnight at room temperature. Filter the mixture and wash the polystyrene resin with 1:1 CH2Cl2/MeOH. Subject the mixture to flash column chromatography (12 g column, eluting with 10% 2M NH3 in MeOH/CH2Cl2) to yield the product as a yellow-white solid (0.040 g, 57%). mass spectrum (m/e): 459.0 (M+1), 457.0 (M−1). 1H NMR (400 MHz, CDCl3): δ 7.75 (d, J=15.2 Hz, 1H), 7.61 (m, 4H), 7.53 (d, J=12.4 Hz, 2H), 7.37 (d, J=8.0 Hz, 1H), 7.20 (d, J=8.0 Hz, 1H), 6.64 (d, J=15.6 Hz, 1H), 3.62-3.49 (m, 2H), 3.20 (s, 3H), 2.77-2.55 (m, 4H), 2.44-2.37 (m, 1H), 2.38 (s, 3H), 2.09-1.98 (m, 1H), 1.63-1.53 (m, 1H).

Provenance & Evidence