Hydrochloric Acid → HCID 23143307, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-(4-{[4-(chloromethyl)benzyl]-oxy}phenyl)propanoate (50 mg, 0.16 mmol) in N,N-dimethylformamide (1 mL) were added a solution of 4-(4-chlorophenyl)-N-ethyl-5-methyl-1,3-oxazole-2-amine (45 mg, 0.19 mmol) in N,N-dimethylformamide (0.5 mL) and potassium carbonate (33 mg, 0.24 mmol), and the mixture was stirred at 70° C. for 66 hr. Water (2 mL) was added to the reaction mixture and the mixture was extracted with dichloromethane (2 mL). The organic layer was concentrated under reduced pressure with a centrifugal concentration apparatus (GeneVac). The obtained resultant product was dissolved in methanol (2 mL), 1N aqueous sodium hydroxide solution (0.32 mL, 0.32 mmol) was added, and the mixture was stirred at room temperature for 18 hr. The reaction mixture was acidified with 1N hydrochloric acid, and extracted with dichloromethane (2 mL). The organic layer was concentrated under reduced pressure with a centrifugal concentration apparatus (GeneVac). The residue was purified by preparative HPLC (gradient cycle B) to give the title compound (4.6 mg, yield 5%).

Provenance & Evidence