4-Methyl-piperazine-1-carboxylic acid methyl-(4-nitro-3-piperidin-1-yl-phenyl)-amide → 4-Methyl-piperazine-1-carboxylic acid (4-amino-3-piperidin-1-yl-phenyl)-methyl-amide

Participants

Reaction Steps

Using a procedure similar to Example 23, step (a), 4-methyl-piperazine-1-carboxylic acid methyl-(4-nitro-3-piperidin-1-yl-phenyl)-amide (110 mg, 0.3 mmol, as prepared in the previous step) was stirred in MeOH in the presence of 5% Pd—C (65 mg) to afford crude 4-methyl-piperazine-1-carboxylic acid (4-amino-3-piperidin-1-yl-phenyl)-methyl-amide as an oil, which in a manner similar to Example 4, step (c) was coupled to 5-cyano-furan-2-carbonyl chloride (64.6 μL, 412 mmol) in the presence of DIEA (115 μL, 0.6 mmol) using a procedure similar to Example 2 to afford 54.4 mg (40%) of the title compound as a bright yellow solid. 1H-NMR (CDCl3, 400 MHz): δ 9.62 (s, 1H), 8.41 (d, 1H, J=8.5 Hz), 7.29 (d, 1H, J=3.8 Hz), 7.24 (d, 1H, J=3.8 Hz), 6.95-6.92 (m, 2H), 3.24-3.26 (M, 4H), 3.22 (s, 3H), 2.84-2.82 (m, 4H), 2.21-2.26 (m, 7H), 1.84-1.79 (m, 4H), 1.66 (m, 2H); Mass spectrum (ESI, m/z): Calcd. for C24H30N6O3, 451.2 (M+H), found 451.1.

Provenance & Evidence