Hydrochloric Acid → HCID 59559605, compound

Participants

Reaction Steps

DIPEA (125 mg, 0.17 mL, 0.97 mmol) was added drop wise to 3,5-dichloro-benzoic acid (74 mg, 0.389 mmol) in DMF (5 mL). EDCI (74 mg, 0.389 mmol) and HOBT (52 mg, 0.389 mmol) were added consecutively and, after 10 minutes, N-(2-Oxo-2-piperazin-1-yl-ethyl)-4-phenylamino-benzamide in its HCl salt form (110 mg, 0.32 mmol) was added. The resulting mixture was stirred at room temperature overnight. Cold water was then added and the product was extracted with EtOAc and the organic layer was washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to get the residue. The obtained residue was purified by column chromatography (using silica gel of 60-120 mesh and 50% EtOAc in Hexane as eluent) to afford 39 mg (15% yield) of N-{2-[4-(3,5-Dichloro-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-4-phenylamino-benzamide. LC-MS purity: 95.72%. 1H-NMR (DMSO-d6): δ 8.6 (s, 1H), 8.3 (t, 1H), 7.8 (d, 3H), 7.5 (s, 2H), 7.3 (t, 2H), 7.2 (d, 2H), 7.1 (d, 2H), 6.9 (t, 1H), 4.1 (m, 2H), 3.6 (m, 2H).

Provenance & Evidence