1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Tert-butyl 4-(6-(5-(3-fluoro-2-(2-hydroxy-2-phenylpentylcarbamoyl)pyridin-4-ylthio)thiazol-2-ylamino)pyridin-3-ylamino)piperidine-1-carboxylate

Participants

Reaction Steps

To a stirring solution of 4-(2-(5-(1-(tert-butoxycarbonyl)piperidin-4-ylamino)pyridin-2-ylamino)thiazol-5-ylthio)-3-fluoropicolinic acid (586 mg, 1.072 mmol), 1-amino-2-phenylpentan-2-ol (479 mg, 2.672 mmol), EDAC (621 mg, 3.239 mmol), HOBt (235 mg, 1.739 mmol) in NMP (7 mL) was added i-Pr2NEt (0.93 mL, 5.339 mmol) and stirred overnight. LCMS showed complete reaction, which was poured into ˜50 mL water and a solid precipitated. The solid was collected by filtration, washed with water and was allowed to air dry. The product was obtained (838 mg, 100%) as a solid: LC/MS (M+H)+: 708. HPLC ret. time (Condition M): 1.95 min.

Provenance & Evidence