Hexane → 4-Cyclohexyl-n-{2-[methyl-(1-methyl-pyrrolidin-3-ylmethyl)-amino]-benzooxazol-5-yl}-benzamide

Participants

Reaction Steps

Combine rac-N2-methyl-N2-(1-methyl-pyrrolidin-3-ylmethyl)-benzooxazole-2,5-diamine (0.040 g, 0.154 mmol), 4-cyclohexylbenzoic acid (0.047 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 a colorless oil. The oil was dissolved in CH2Cl2 and hexane added. The mixture was concentrated and dried under high vacuum to yield the desired product as a white solid (0.034 g, 50%). mass spectrum (m/e): 447.3 (M+1). 1H NMR (400 MHz, CD3OD): δ 7.89-7.85 (m, 2H), 7.71 (d, J=2.0 Hz, 1H), 7.39-7.28 (m, 4H), 3.59 (m, 2H), 3.23 (s, 3H), 2.83-2.58 (m, 6H), 2.39 (s, 3H), 2.13-2.01 (m, 1H), 1.94-1.84 (m, 4H), 1.83-1.76 (m, 1H), 1.67-1.57 (m, 1H), 1.57-1.41 (m, 4H), 1.40-1.28 (m, 1H).

Provenance & Evidence