1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57874453, compound

Participants

Reaction Steps

DIPEA (180 mg, 1.47 mmol) was added to a stirred solution of 1 4-(5-methyl-[1,3,4]oxadiazol-2-yl)-benzoic acid (100 mg, 0.48 mmol) in DMF (2 mL) followed by HOBt (79 mg, 0.58 mmol) and EDCI (113 mg, 0.587 mmol). After 2 minutes of stirring, 2-amino-1-[4-(2-chloro-phenoxy)-piperidin-1-yl]-ethanone hydrochloride (179 mg, 0.587 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 The residue was purified by preparative HPLC to afford 50 mg (22.52% Yield) of N-{2-[4-(2-chloro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-4-(5-methyl-[1,3,4]oxadiazol-2-yl)-benzamide. LC/MS [M+H]+: 93.97%. 1H NMR (300 MHz, DMSO-d6): δ 8.8 (s, 1H), 8.2-7.9 (m, 4H), 7.5-7.2 (m, 3H), 7.0 (bt, 1H), 4.8 (bs, 1H), 4.2 (bs, 2H), 3.7 (bs, 2H), 3.5 (m, 2H), 2.7-2.5 (m, 3H), 2.1-1.5 (m, 4H).

Provenance & Evidence