Diisopropylethylamine → 5-Cyano-furan-2-carboxylic Acid (3-chloro-2-piperidin-1-yl-phenyl)-amide

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Reaction Steps

Using a procedure similar to Example 3, step (d), 3-chloro-2-piperidin-1-yl-phenylamine (54 mg, 0.25 mmol, as prepared in the previous step) was allowed to react with 5-cyano-furan-2-carbonyl chloride (55.8 mg, 0.360 mmol) in the presence of DIEA (95 μL, 0.55 mmol) to afford 8.4 mg (10%) of the title compound as a yellow solid. 1H-NMR (CDCl3; 400 MHz): δ 10.70 (br s, 1H), 8.42 (dd, 1H, J=1.4, 8.1 Hz), 7.30 (dd, J=1.5, 3.7 Hz), 7.24 (d, 1H, J=3.7 Hz), 7.17 (t, 1H, J=8.1 Hz), 7.07 (dd, 1H, J=1.4, 8.1 Hz), 3.58-3.52 (m, 2H), 2.85-2.82 (m, 2H), 2.02-1.99 (m, 1H), 1.89-1.72 (m, 4H), 1.52-1.38 (m, 1H), Mass spectrum (ESI, m/z): Calcd. for C17H16ClN3O2, 330.0 (M+H), found 330.1.

Provenance & Evidence