1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178425533, compound

Participants

Reaction Steps

DIPEA (193.9 mg, 1.5 mmol) followed by HOBt (53 mg, 0.29 mmol) and EDCI (75 mg, 0.39 mmol) was added to a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (92 g, 0.37 mmol) in DMF (3 mL) After 2 minutes of stirring, 3-(azetidin-3-yloxy)-4-methyl-benzonitrile hydrochloride (prepared by the method used for the synthesis of Intermediate 71) (84 mg, 0.37 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 35 mg (22.5% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[3-(5-cyano-2-methyl-phenoxy)-azetidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 416, 92.49%. 1H NMR (300 MHz, DMSO-d6): δ 13.8 (s, 1H), 8.2 (t, 1H), 7.74 (t, 2H), 7.42 (m, 2H), 7.3 (m, 3H), 7.16 (s, 1H), 7.08 (s, 1H), 5.2 (m, 1H), 4.7 (m, 1H), 4.4 (m, 1H), 4.2 (m, 1H), 3.8 (m, 3H).

Provenance & Evidence