Oxalyl chloride → HCID 11606279, compound

Participants

Reaction Steps

The procedure of Example 4, step (c) was followed using 156 mg (0.348 mmol) of carbonic acid tert-butyl ester 2-{4-[3-(4-methyl-piperidin-1-yl)-4-nitro-phenyl]-piperazin-1-yl}-ethyl ester (as prepared in the previous step), 78 mg of 10% palladium on carbon (50% by weight water), 52.5 mg (383 mmol) of 5-cyanofuran-2-carboxylic acid (as prepared in Example 1), 50.1 μL (0.575 mmol) of oxalyl chloride, and 121 μL (0.696 mmol) of DIEA. Chromatography on a 10-g silica SPE column with 5-20% EtOAc-dichloromethane afforded 176 mg (94%) of the title compound as a light yellow solid: 1H-NMR (CDCl3; 400 MHz): δ 9.60 (br s, 1H), 8.29 (d, 1H, J=8.9 Hz), 7.21, 7.24 (AB q, 2H, J=3.7 Hz), 6.79 (d, 1H, J=2.6 Hz), 6.71 (dd, 1H, J=8.9, 2.6 Hz), 4.23 (t, 2H, J=5.8 Hz), 3.16-3.19 (m, 4H), 2.97-3.00 (m, 2H), 2.67-2.75 (m, 8H), 1.82-1.84 (m, 4H), 1.50-1.65 (m, 1H), 1.46-1.58 (m, 2H, partially obscured by t-Bu peak), 1.49 (s, 9H), and 1.07 (d, 3H, J=6.2 Hz). Mass spectrum (ESI, m/z): Calcd. for C29H39N5O5, 538.3 (M+H) and 438.2 (M-BOC+2H), found 538.2, 438.2.

Provenance & Evidence