1,2-Dichloroethane → N-[(1R)-1-(5-bromo-1,3-thiazol-2-yl)ethyl]-2-[4-(propan-2-yl)phenyl]acetamide

Beteiligte Stoffe

Reaktionsschritte

To a solution of 0.050 g (0.28 mmol) 4-isopropylphenyl acetic acid in 0.50 mL DMF and 1.0 mL CH2Cl2 was added 0.072 g (0.30 mmol) (1R)-1-(5-bromo-1,3-thiazol-2-yl)ethanamine hydrochloride, 0.042 g (0.31 mmol) HOAT, 0.059 g (0.31 mmol) EDC, and 0.093 mL (0.56 mmol) DIEA. After 1 h at room temperature, the reaction mixture was purified by preparative reverse-phase HPLC (5->95% CH3CN/H2O over 15 min, 0.05% added TFA, C18) to give N-[(1R)-1-(5-bromo-1,3-thiazol-2-yl)ethyl]-2-[4-(propan-2-yl)phenyl]acetamide. 1H NMR (CDCl3, 400 MHz) δ 7.54 (s, 1H); 7.59 (ABq, J=8.4 Hz, 4H), 6.55 (br d, J=7.6 Hz, 1H), 5.32 (quintet, J=7.2 Hz, 1H), 3.59 (s, 2H), 2.91 (m, J=7.2 Hz, 3H); 1.52 (d, J=7.2 Hz, 3H), 1.25 (d, J=7.2 Hz, 6H). HRMS (ES) [M+1]+ calcd for C16H19BrN2OS: 367.0474. Found: 367.0483.

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