2-amino-5-[4-(difluoromethoxy)phenyl]-5-[3-(3-methoxyprop-1-yn-1-yl)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one → 2-Amino-5-[4-(difluoromethoxy)phenyl]-5-[3-(3-methoxypropyl)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one

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Reaction Steps

A mixture of an ethanolic solution of 2-amino-5-[4-(difluoromethoxy)phenyl]-5-[3-(3-methoxyprop-1-yn-1-yl)phenyl]-3-methyl-3,5-dihydro-4H-imidazol-4-one (0.1 g, 0.25 mmol) and 10% palladium on charcoal (10 mg) was placed under a hydrogen filled balloon for 16 h and filtered thru celite. The filtrate was concentrated to dryness in vacuo. The resultant residue was purified by flash chromatography on silica gel, ethyl acetate as eluent, to give the title product as a white solid, 0.04 g (40% yield), mp 48-50° C.; 1H NMR (DMSO-d6) δ 2.4 (m, 2H); 2.95 (s, 3H); 3.2 (s, 3H); 3.3 (t, 2H); 6.6 (b, 2H); 7.1 (m, 3H); 7.2 (m, 4H); 7.4 (d, 2H); MS [(+)ESI] m/z=404 [M−H]+.

Provenance & Evidence