Picolinic acid → Pyridine-2-carboxylic Acid [2-((S)-2-imidazol-1-yl-1-phenyl-ethoxy)-5-oxo-5,6,7,8-tetrahydro-naphthalen-1-yl]-amide

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Reaction Steps

To a solution of 5-amino-6-((S)-2-imidazol-1-yl-1-phenyl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one (150 mg, 0.432 mmol), picolinic acid (64 mg, 0.518 mmol) and HOBT (73 mg, 0.540 mmol) in DMF (4 mL) was added N-methylmorpholine (62 μL, 0.562 mmol) followed by EDCI HCl (108 mg, 0.562 mmol). After 2 days, the DMF was removed under reduced pressure. The residue was partitioned between EtOAc and H2O. The organic layer was washed with H2O and brine, dried over Na2SO4 and concentrated to give a brown oil. Purification by chromatography (3-5% MeOH/CH2Cl2) afforded the title compound as a tan foam (160 mg, 0.354 mmol, 82%). The structure was confirmed by NMR and mass spectrometry. MS m/z 453 (M++H).

Provenance & Evidence