Pentanoyl chloride, 4-methyl- → {4-[2-Fluoro-4-(4-methyl-pentanoylamino)-phenyl]-piperazin-1-yl}-phenyl-acetic acid methyl ester

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Reaction Steps

A solution of [4-(4-amino-2-fluoro-phenyl)-piperazin-1-yl]-phenyl-acetic acid methyl ester (35 mg, 0.10 mmol) in DCM (2 mL) was treated with 4-methylvaleroyl chloride (15 mg, 0.11 mmol) followed by TEA (16 μL, 0.11 mmol). After 16 h, the mixture was purified directly by PTLC to give a beige solid (33 mg, 73%). MS (ESI): mass calcd. for C25H32FN3O3, 441.55; m/z found, 442.5 [M+H]+. 1H NMR (CDCl3): 7.46-7.44 (m, 2H), 7.42-7.39 (m, 1H), 7.36-7.32 (m, 3H), 7.05-7.03 (m, 1H), 6.98 (br s, 1H), 6.88-6.84 (m, 1H), 4.06 (s, 1H), 3.70 (s, 3H), 3.10-3.06 (m, 4H), 2.34-2.31 (m, 4H), 2.35-2.31 (m, 2H), 1.62-1.60 (m, 3H), 0.92 (d, J=6.1, 6H).

Provenance & Evidence