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

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Reaction Steps

Add oxalyl chloride (0.20 mL, 2.30 mmol) and 3 drops of DMF to a stirring suspension of 3-(4-trifluoromethyl-phenyl)-acrylic acid (0.249 g, 1.15 mmol) in CH2Cl2 (5.0 mL). Stir the reaction mixture at room temperature for 2 h. Concentrate the mixture in vacuo, add n-hexane, re-concentrate, and re-dissolve in CH2Cl2. Add the resultant 3-(4-trifluoromethyl-phenyl)-acryloyl chloride solution to a mixture of rac-N2-methyl-N2-(1-methyl-piperidin-4-yl)-benzooxazole-2,5-diamine (0.158 g, 0.607 mmol) and pyridine (0.06 mL) in CH2Cl2 (5.0 mL). Shake the reaction mixture overnight at room temperature. Filter the reaction mixture and wash the product with CH2Cl2. Dry the product on high vacuum to yield the desired product as an off-white solid (0.321 g, 91%). mass spectrum (m/e): 459.0 (M+1), 457.0 (M−1). 1H NMR (400 MHz, CD3OD): δ 8.93-8.89 (m, 1H), 8.71 (dt, J=8.0, 1.8 Hz, 1H), 8.17-8.13 (m, 1H), 7.85-7.72 (m, 4H), 7.55 (d, J=8.8 Hz, 1H), 7.44 (dd, J=8.8, 1.8 Hz, 1H), 6.94 (d, J=15.8 Hz, 1H), 4.57-4.47 (m, 1H), 3.75-3.67 (m, 2H), 3.36-3.29 (m, 2H), 3.28 (s, 3H), 2.96 (s, 3H), 2.41-2.28 (m, 2H), 2.27-2.18 (m, 2H).

Provenance & Evidence