Ammonia methanol → 2-[3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-4-methyl-oxazole-5-carboxylic acid amide

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Reaction Steps

The above 2-[2-acetoxymethyl-3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-phenyl]-4-methyl-oxazole-5-carboxylic acid ethyl ester was dissolved in 10 mL of NH3/MeOH. The reaction was stirred at room temperature for two days. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography (petroleum ether/ethyl acetate=1:1) to give 2-[3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-4-methyl-oxazole-5-carboxylic acid amide (47 mg, yield 68% for two steps) as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 8.57 (s, 1H), 8.24 (d, J=8.1 Hz, 1H), 8.20 (dd, J=2.1, 8.4 Hz, 1H), 8.06-8.00 (m, 2H), 7.66-7.58 (m, 2H), 4.73-4.57 (m, 2H), 2.46 (s, 3H), 1.41 (s, 9H). LC-MS calcd for C24H24N4O4 (m/e) 432.18, obsd 433 [M+H]+.

Provenance & Evidence