1,2-Dichloroethane → 2-(4-isopropylphenyl)-N-[(1R)-1-(5-methoxypyridin-2-yl)ethyl]acetamide

Beteiligte Stoffe

Reaktionsschritte

To a suspension of 4-isopropylphenylacetic acid (2.5 g, 14.0 mmol), (1R)-1-(5-methoxypyridin-2-yl)ethylamine hydrochloride (3.2 g, 16.8 mmol), EDC (3.24 g, 16.9 mmol), and 1-hydroxy-7-azabenzotriazole (2.3 g, 16.8 mmol) in DMF (60 mL) was added N,N-diisopropylethylamine (5.2 mL, 29.6 mmol). The reaction mixture was stirred at room temperature for 2.5 h and then concentrated to 20 mL and diluted with CH2Cl2 (100 mL). The solution was washed with water (100 mL) and the aqueous layer was extracted with CH2Cl2 (2×75 mL). The combined organic layer was washed with water (100 mL), dried over MgSO4, concentrated and purified by normal phase chromatography (10-100% EtOAc/Hexanes) to give of 2-(4-isopropylphenyl)-N-[(1R)-1-(5-methoxypyridin-2-yl)ethyl]acetamide as a pale yellow solid. 1H NMR (CDCl3, 400 MHz) δ 8.14 (d, J=2.56 Hz, 1H), 7.20 (m, 4H), 7.13 (m, 2H), 6.69 (d, J=6.78 Hz, 1H), 5.08 (quint., J=6.96 Hz, 1H), 3.84 (s, 3H), 3.55 (s, 2H), 2.90 (sept., J=6.96 Hz, 1H), 1.39 (d, J=6.77 Hz, 3H), 1.25 (d, J=6.96 Hz, 6H); MS (Electrospray): m/z 313.4 (M+H).

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