Trifluoroacetic acid → HCID 11533182, compound

Participants

Reaction Steps

To a mixture of 4-cyano-1H-pyrrole-2-carboxylic acid [2-(4-methyl-piperidin-1-yl)-4-piperidin-4-yl-phenyl]-amide bis(trifluoroacetic acid salt) (as prepared in Example 35, 20.0 mg, 0.0320 mmol) and anh Na2CO3 (6.8 mg, 0.065 mmol) in 0.30 mL of DMF was added carbonyldiimidazole (11 mg, 0.068 mmol) in 0.3 mL of THF at RT. The mixture was stirred at RT for 2 h. Treated with 20 mL of EtOAc, the mixture was washed with H2O, brine and dried with Na2SO4. Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (1-5% MeOH/DCM) gave 14 mg (86%) of the title compound as a white solid: 1H-NMR (CDCl3; 400 MHz): δ 10.7 (s, 1H), 9.16 (s, 1H), 8.33 (d, 1H, J=8.3 Hz), 7.95 (s, 1H), 7.47 (s, 1H), 7.13 (s, 1H), 7.06 (s, 1H), 7.03 (s, 1H), 6.88 (s, 1H), 4.28 (d, 2H, J=12.9 Hz), 3.16 (d, 2H, J=12.0 Hz), 2.97 (d, 2H, J=11.6 Hz), 2.71-2.84 (m, 3H), 1.99 (d, 2H, J=12.1 Hz), 1.87 (d, 2H, J=12.1 Hz), 1.71-1.83 (m, 2H), 1.65 (s, 1H), 1.54-1.65 (m, 1H), 1.34-1.48 (m, 2H), 1.10 (d, 3H, J=6.5 Hz). Mass spectrum (ESI, m/z): Calcd. for C27H31N7O2, 486.2 (M+H), found 486.0.

Provenance & Evidence