1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57874481, compound

Participants

Reaction Steps

DIPEA (195 mg, 1.66 mmol) was added to a stirred solution of 1-(5-fluoro-pyridin-3-yl)-1H-[1,2,3]triazole-4-carboxylic acid (70 mg, 0.33 mmol) (prepared by the method used for the synthesis of Intermediate 64, starting from 3-amino-5-fluoropyridine) in DMF (5 mL) followed by HOBt (55 mg, 0.41 mmol) and EDCI (177 mg, 0.92 mmol). After 2 minutes of stirring, 2-amino-1-[4-(2-chloro-phenoxy)-piperidin-1-yl]-ethanone hydrochloride (prepared according to Step 1 and 5 of the General Scheme) (124 mg, 0.4 mmol) was added and the resulting mixture was stirred at ambient temperature overnight. Cold water was then added and the solid was collected to afford 147 mg (90.74% Yield) of 1-(5-fluoro-pyridin-3-yl)-1H-[1,2,3]triazole-4-carboxylic acid {2-[4-(2-chloro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 441 (M+1), 98.31%. 1H NMR (300 MHz, DMSO-d6): δ 9.5 (s, 1H), 9.24 (d, 1H), 8.76 (d, 1H), 8.56 (t, 1H), 8.46 (d, 1H), 7.74 (d, 1H), 7.48 (d, 1H), 7.36 (q, 2H), 7.02 (t, 1H), 4.8 (m, 1H), 4.4 (d, 2H), 3.8 (t, 2H), 3.6 (t, 2H), 2.1 (d, 2H), 1.8 (d, 2H).

Provenance & Evidence