Diisopropylethylamine → N-[1-(2-methoxyethyl)pyrazol-4-yl]-2-[4-(6,7-dimethoxyquinolin-4-yloxy)phenyl]acetamide

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Reaction Steps

Diisopropylethylamine (0.124 ml) and 2-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate(V) (0.247 g) were added in turn to a stirred mixture of 2-[4-(6,7-dimethoxyquinolin-4-yloxy)phenyl]acetic acid (0.2 g), 4-amino-1-(2-methoxyethyl)pyrazole (0.092 g) and DMF (3 ml) and the resultant mixture was stirred at ambient temperature for 18 hours. The resultant mixture was evaporated and the residue was purified by column cliromatography on silica using a solvent gradient from 100:0 to 24:1 mixtures of methylene chloride and a 3.5M methanolic ammonia solution as eluent. There was thus obtained the title compound as a solid (0.106 g); 1H NMR: (DMSOd6) 3.21 (s, 3H), 3.62 (s, 2H), 3.63 (t, 2H), 3.92 (s, 3H), 3.94 (s, 3H), 4.12 (t, 2H), 6.47 (d, 1H), 7.22 (d, 2H), 7.4 (s, 1H), 7.44 (s, 1H), 7.45 (d, 2H), 7.49 (s, 1H), 7.89 (s, 1H), 8.47 (d, 1H), 10.2 (s, 1H); Mass Spectrum: M+H+ 463.

Provenance & Evidence