Dimethylformamide → N-(3-methoxyphenyl)-2-[4-(6,7-dimethoxyquinazolin-4-yloxy)phenyl]acetamide

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Reaction Steps

Diisopropylethylamine (0.073 ml) and 2-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate(V) (0.16 g) were added in turn to a stirred mixture of 2-[4-(6,7-dimethoxyquinazolin-4-yloxy)phenyl]acetic acid (0.12 g), 3-methoxyaniline (0.047 ml) and DMF (3 ml) and the resultant mixture was stirred at ambient temperature for 2 hours. Water was added and the precipitate was recovered by filtration and purified by column chromatography on silica using a 19:1 mixture of methylene chloride and methanol as eluent. There was thus obtained the title compound as a solid (0.122 g); 1H NMR: (DMSOd6) 3.69 (s, 2H), 3.73 (s, 3H), 3.97 (s, 3H), 3.99 (s, 3H), 6.63 (m, 1H), 7.15 (d, 1H), 7.21 (m, 1H), 7.26 (d, 2H), 7.34 (m, 1H), 7.39 (s, 1H), 7.43 (d, 2H), 7.55 (s, 1H), 8.54 (s, 1H), 10.21 (s, 1H); Mass Spectrum: M+H+ 446.

Provenance & Evidence