Pyridine → 4-Cyclohexyl-n-{2-[methyl-(1-methyl-piperidin-4-yl)-amino]-benzooxazol-5-yl}-benzamide

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Reaction Steps

Add oxalyl chloride (0.16 mL, 1.82 mmol) and 3 drops of DMF to a stirring suspension of 4-cyclohexyl-benzoic acid (0.197 g, 0.910 mmol) in CH2Cl2 (2.0 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 4-cyclohexyl-benzoyl 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 (0.05 mL) in CH2Cl2 (10 mL). Shake the reaction mixture overnight at room temperature. Wash the mixture with saturated NaHCO3 (aqueous) (2×20 mL), dry the organic phase over Na2SO4, filter, and concentrate the mixture in vacuo. Subject the residue to silica gel flash column chromatography (3×4 g columns, eluting with 5% 2N NH3 in MeOH/CH2Cl2) to yield the desired product as a white solid (0.169 g, 62%). mass spectrum (m/e): 447.3 (M+1). 1H NMR (400 MHz, CDCl3): δ 7.85 (s, 1H), 7.78 (d, J=8.4 Hz, 2H), 7.47 (d, J=2.0 Hz, 1H), 7.35 (dd, J=8.8, 2.0 Hz, 1H), 7.31-7.27 (m, 2H), 7.19 (d, J=8.8 Hz, 1H), 4.19-4.10 (m, 1H), 3.06 (s, 3H), 2.96 (d, J=12.0 Hz, 2H), 2.66-2.50 (m, 1H), 2.31 (s, 3H), 2.15 (dt, J=11.6, 2.4 Hz, 2H), 1.98-1.71 (m, 10H), 1.48-1.33 (m, 3H), 1.31-1.19 (m, 1H).

Provenance & Evidence