Oxalyl chloride → 5-cyano-N-(4-(4-methylpiperazin-1-yl)-2-(4-methylpiperidin-1-yl)phenyl)furan-2-carboxamide

Participants

Reaction Steps

The procedure of Example 4, step (c) was followed using 50.2 mg (0.158 mmol) of 1-methyl-4-[3-(4-methyl-piperidin-1-yl)-4-nitro-phenyl]-piperazine (as prepared in the previous step), 20 mg of 10% palladium on carbon (50% by weight water), 22.8 mg (0.166 mmol) of 5-cyanofuran-2-carboxylic acid (as prepared in Example 1), 29.0 μL (0.332 mmol) of oxalyl chloride, and 57.8 μL (0.332 mmol) of DIEA. Chromatography on a 5-g silica SPE column with 0.5-3% MeOH-dichloromethane afforded 34.8 mg (54%) of the title compound as a light yellow solid: 1H-NMR (CDCl3; 400 MHz): o 9.59 (br s, 1H), 8.33 (d, 1H, J=8.9 Hz), 7.21, 7.25 (AB q, 2H, J=3.7 Hz, partially obscured by CHCl3 peak), 6.78 (d, 1H, J=2.7 Hz), 6.74 (dd, 1H, J=8.9, 2.7 Hz), 3.35-3.55 (m, 4H), 2.95-3.05 (m, 4H), 2.72-2.75 (m, 4H), 2.67 (br s, 3H), 1.83-1.87 (m, 2H), 1.45-1.65 (br m, 1H), 1.43-1.53 (m, 2H) and 1.07 (d, 3H, J=6.2 Hz), Mass spectrum (ESI, m/z): Calcd. for C23H29N5O2, 408.2 (M+H), found 408.3.

Provenance & Evidence