1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-{2-[4-(2-chloro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-4-[1,3,4]oxadiazol-2-yl-benzamide

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Reaction Steps

DIPEA (203 mg, 0.27 mL, 1.57 mmol) was added to a stirred solution of 4-[1,3,4]oxadiazol-2-yl-benzoic acid (100 mg, 0.52 mmol) in DMF (2 mL) followed by HOBt (85 mg, 0.63 mmol) and EDCI (121 mg, 0.63 mmol). After 2 minutes of stirring, 2-amino-1-[4-(2-chloro-phenoxy)-piperidin-1-yl]-ethanone hydrochloride (192 mg, 0.63 mmol) (prepared according to Step 1 and 5 of the General Scheme) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and the product was extracted with EtOAc and the organic layer was washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to afford 88 mg (38.09% yield) of N-{2-[4-(2-chloro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-4-[1,3,4]oxadiazol-2-yl-benzamide. LC/MS [M+H]+: 441.13, 95.23%. 1H NMR (300 MHz, DMSO-d6): δ 9.4 (s, 1H), 8.8 (t, 1H), 8.1 (q, 4H), 7.4 (m, 1H), 7.3 (m, 2H), 7.0 (m, 1H), 4.8 (m, 1H), 4.2 (m, 2H), 3.7 (m, 2H), 3.5 (m, 2H), 2.18 (m, 2H), 1.8-1.5 (m, 4H).

Provenance & Evidence