1-Hydroxy-2-naphthoic acid → [5-tert-Butoxycarbonylamino-1-(6-chloro-5-(4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-phenylcarbamoyl)-pyridazin-3-yl)-piperidin-3-yl]-carbamic acid tert-butyl ester

Participants

Reaction Steps

iPr2NEt (360 μL, 2 mmol) in THF (1 ml) was added to a mixture of 207 (483 mg, 1.02 mmol) and 1-hydroxy-naphthalene-2-carboxylic acid 111 (4-amino-phenyl)-amide (283.88 mg, 1.02 μmol) in THF (5 mL). HOBT (306.3 mg, 2 mmol) in THF (2 mL) was added. The reaction mixture was vortexed for 1 minute. EDCI (383.4 mg, 2 mmol) in CH2Cl2 (4 mL) was added into the above reaction mixture. The reaction mixture was shaken at room temperature for 16 h. The solvent was removed under reduced pressure. The solid was dissolved in CHCl3 (5 mL), washed with 10% NaHCO3 (3 mL), H2O (3 mL) and dried over MgSO4. Solvent was removed under reduced pressure. After flash chromatography purification using ethyl acetate and hexane, 730 mg of compound 209 (98.4% yield) was obtained as a solid. LC-MS (ESI): m/z=732.5 [M+1]+.

Provenance & Evidence