4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-(1,1-dioxo-hexahydro-1lambda6-thiopyran-4-yl)-2-(4-methyl-piperidin-1-yl)-phenyl]-amide → HCID 178428186, compound

Participants

Reaction Steps

A solution of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-2-(4-methyl-piperidin-1-yl)-phenyl]-amide (as prepared in the previous step, 19.0 mg, 0.0330 mmol) in 1 mL of 2:1 TFA/DCM was stirred at RT for 4 h. Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (10-20% EtOAc/DCM) gave 13.2 mg (90%) of the title compound as a white solid: 1H-NMR (CDCl3; 400 MHz): δ 12.00 (s, 1H), 10.29 (s, 1H), 8.33 (d, 1H, J=8.3 Hz), 7.76 (d, 1H, J=2.3 Hz), 7.12 (dd, 1H, J=8.3, 1.7 Hz), 7.06 (d, 1H, J=1.7 Hz), 3.14-3.22 (m, 4H), 3.01 (d, 2H, J=12.0 Hz), 2.68-2.83 (m, 3H), 2.38-2.53 (m, 2H), 2.23 (d, 2H, J=14.5 Hz), 1.50-1.85 (m, 5H), 1.09 (d, 3H, J=5.8 Hz). Mass spectrum (ESI, m/z): Calcd. for C22H27N5O3S, 442.2 (M+H), found 442.2.

Provenance & Evidence