1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 53361692, compound

Participants

Reaction Steps

To a solution of (E)-3-[3-chloro-4-({5-[(4-fluorobenzyl)oxy]pyridin-2-yl}oxy)phenyl]prop-2-enoic acid (212 mg) in DMF (7.0 mL) were added 1-{4-[2-(3-methoxyphenoxy)ethyl]benzyl}piperazine (190 mg), HOBT (89 mg) and WSC (112 mg) at room temperature, then the reaction mixture was stirred over night. The reaction mixture was basified with saturated aqueous NaHCO3, extracted with AcOEt. The organic layer was washed with water and saturated aqueous NaCl, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=1/4 to 0/1 and then MeOH/AcOEt=1/9) to afford (E)-3-[3-chloro-4-({5-[(4-fluorobenzyl)oxy]pyridin-2-yl}oxy)phenyl]-1-(4-{4-[2-(3-methoxyphenoxy)ethyl]benzyl}-piperazin-1-yl)prop-2-en-1-one (387 mg) as a colorless amorphous. To a solution of that amorphous (387 mg) in AcOEt (7.0 mL) was added 6 M aqueous HCl (0.088 mL) at room temperature, and then the reaction mixture was stirred for 30 minutes. The reaction mixture was filtered off, and the crude crystal was recrystallized from EtOH—H2O to afford (E)-3-[3-chloro-4-({5-[(4-fluorobenzyl)oxy]pyridin-2-yl}oxy)phenyl]-1-(4-{4-[2-(3-methoxyphenoxy)ethyl]benzyl}piperazin-1-yl)prop-2-en-1-one hydrochloride as a colorless powder (333 mg).

Provenance & Evidence