N-Methyl-N-(4-nitro-3-piperidin-1-yl-phenyl)-acetamide → n-(4-Amino-3-piperidin-1-yl-phenyl)-n-methyl-acetamide

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Reaction Steps

Using a procedure similar to Example 3, step (c), N-methyl-N-(4-nitro-3-piperidin-1-yl-phenyl)-acetamide (67 mg, 0.24 mmol, as prepared in the previous step) was stirred with 5% Pd—C (45 mg) under H2 to afford N-(4-amino-3-piperidin-1-yl-phenyl)-N-methyl-acetamide which was used immediately. Using a procedure similar to Example 3, step (d) this was coupled to 5-cyano-furan-2-carbonyl chloride (52 mg, 0.33 mmol) in the presence of DIEA (107 μL, 0.55 mmol) to afford 7.3 mg (8%) of the title compound as a waxy solid. 1H-NMR (CDCl3; 400 MHz): δ 9.66 (s, 1H), 8.48 (d, 1H, J=9.2 Hz), 7.34 (d, 1H, J=3.7 Hz), 7.26 (d, 1H, J=3.3 Hz), 7.03-7.01 (m, 2H), 3.27 (s, 3H,), 2.88-2.86 (m, 4H), 1.90 (s, 3H), 1.88-1.82 (m, 4H), 1.63 (br s, 2H); Mass spectrum (ESI, m/z): Calcd. for C20H22N4O3, 367.1 (M+1), found 367.2.

Provenance & Evidence