2-Pyridineacetic acid, hydrochloride (1:1) → n-[2-((s)-2-Imidazol-1-yl-1-phenyl-ethoxy)-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-yl]-2-pyridin-2-yl-acetamide

Participants

Reaction Steps

To a solution of 5-amino-6-((S)-2-imidazol-1-yl-1-phenyl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one (100 mg, 0.288 mmol) and 2-pyridylacetic acid HCl (67 mg, 0.386 mmol) in DMF (3 mL) was added EDCI HCl (111 mg, 0.576 mmol, 2 equiv). The yellow solution turned orange overnight. Some of the DMF was removed under reduced pressure. The residue was dissolved in H2O and 1 M NaOH was added until the solution was basic (pH 10). The mixture was extracted thoroughly with CH2Cl2. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give a bright yellow oil. Purification by chromatography (7% MeOH/CH2Cl2) afforded the title compound as a pale yellow foam (107 mg, 0.229 mmol, 80%). The structure was confirmed by NMR and mass spectrometry. MS m/z 467 (M++H).

Provenance & Evidence