Dimethylformamide → 2-(4-{4-[2-(3,5-Dimethyl-isoxazol-4-yl)-acetylamino]-2-fluoro-phenyl}-piperazin-1-yl)-N,N-diethyl-2-phenyl-acetamide

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Reaction Steps

A mixture of (3,5-dimethyl-isoxazol-4-yl)-acetic acid (1.0 mmol) and DMF (0.050 mL) in DCE (10 mL) was treated with (COCl)2 (10 mmol) dropwise, and was stirred at rt for 1 h. The mixture was concentrated and dried under vacuum. The residue was diluted with DCE (10 mL) and 2-[4-(4-amino-2-fluoro-phenyl)-piperazin-1-yl]-N,N-diethyl-2-phenyl-acetamide (0.30 mmol) and TEA (2.0 mmol) were added. The mixture was stirred at rt for 16 h, then was washed with H2O (10 mL). The organic layer was concentrated, and the residue was purified by PTLC to provide the title compound (78 mg, 45%). MS (ESI): mass calcd. for C29H36FN5O3, 521.28. m/z found, 522.4 [M+H]+. 1H NMR (CDCl3): 7.59-7.25 (m, 6H), 7.09-6.98 (m, 1H), 6.68-6.57 (m, 1H), 4.21 (s, 1H), 3.50-3.36 (m, 4H), 3.35-3.15 (m, 2H), 3.13-3.00 (m, 4H), 2.73-2.60 (m, 4H), 2.37 (s, 3H), 2.23 (s, 3H), 1.16-1.06 (m, 6H).

Provenance & Evidence