1-Ethyl-1h-pyrazol-4-amine → N-(1-ethylpyrazol-4-yl)-2-[4-(6-fluoroquinolin-4-yloxy)-2-methoxyphenyl]propionamide

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Reaction Steps

Using an analogous procedure to that described in Example 2, 2-[4-(6-fluoroquinolin-4-yloxy)-2-methoxyphenyl]propionic acid was reacted with 4-amino-1-ethylpyrazole. The resultant mixture was evaporated and the residue was purified by preparative HPLC using a Waters ‘Xterra’ reversed-phase column (5 microns silica, 30 mm diameter, 150 mm length) using decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent. There was thus obtained the title compound as a solid in 39% yield; 1H NMR: (DMSOd6) 1.32 (t, 3H), 1.38 (d, 3H), 3.81 (s, 3H), 4.02-4.11 (m, 3H), 6.7 (d, 1H), 6.85 (m, 1H), 7.0 (d, 1H), 7.38-7.44 (m, 2H), 7.75 (m, 1H), 7.90 (s, 1H), 7.96 (m, 1H), 8.12 (m, 1H), 8.69 (d, 1H), 9.97 (s, 1H); Mass Spectrum: M+H+ 435.

Provenance & Evidence