Hydrochloric Acid → HCID 59559612, compound

Participants

Reaction Steps

DIPEA (114 mg, 0.15 mL, 0.88 mmol) was added drop wise to 2-bromo-5-fluoro-benzoic acid (77 mg, 0.35 mmol) in DMF (5 mL). EDCI (114 mg, 0.88 mmol) and HOBT (47 mg, 0.35 mmol) were added consecutively and, after 10 minutes, N-(2-Oxo-2-piperazin-1-yl-ethyl)-4-phenylamino-benzamide in its HCl salt form (100 mg, 0.29 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 70% EtOAc in Hexane as eluent) to afford 80 mg (50% yield) of N-{2-[4-(2-bromo-5-fluoro-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-4-phenylamino-benzamide. LC-MS purity: 94.48%. 1H-NMR (DMSO-d6): δ 8.6 (s, 1H), 8.3 (t, 1H), 7.8 (d, 3H), 7.4 (m, 4H), 7.2 (d, 2H), 7.1 (d, 2H), 6.9 (t, 1H), 4.1 (dd, 2H), 3.6 (m, 6H), 3.2 (m, 2H).

Provenance & Evidence