1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178523555, compound

Participants

Reaction Steps

DIPEA (143 mg, 1.1 mmol) followed by HOBt (39 mg, 0.29 mmol) and EDCI (56 mg, 0.29 mmol) was added to a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (67 g, 0.27 mmol) in DMF (2 mL). After 2 minutes of stirring, 3-(2-chloro-phenoxy)-azetidinehydrochloride (prepared by the method used for the synthesis of Intermediate 71) (60 mg, 0.27 mmol) was added and the resulting mixture was stirred at room temperature overnight. The reaction mixture was partitioned between cold water and ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. Purification by preparative HPLC afforded 48 mg (42.8% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[3-(2-chloro-phenoxy)-azetidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 411, 99.1%. 1H NMR (300 MHz, DMSO-d6): δ 13.7 (s, 1H), 8.2 (t, 1H), 7.54 (m, 2H), 7.28 (m, 5H), 7.08 (d, 1H), 7.0 (t, 1H), 6.86 (d, 1H), 5.1 (m, 1H), 4.64 (m, 1H), 4.36 (m, 1H), 4.2 (m, 1H), 3.84 (m, 3H).

Provenance & Evidence