Salicyluric Acid → HCID 25165129, compound

Participants

Reaction Steps

DIPEA (0.239 mL, 1.39 mmol) was added drop wise to (2-hydroxy-benzoyl amino)-acetic acid (90 mg, 0.46 mmol) in DMF (7 mL). EDCI (221 mg, 1.15 mmol) and HOBT (74 mg, 0.55 mmol) were added consecutively and after 5 minutes, piperazin-1-yl-(2-trifluoromethyl-phenyl)-methanone (162 mg, 0.55 mmol) was added. The resulting mixture was stirred at room temperature overnight. Water was then added, and the product was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford the crude product. Purification using column chromatography (silica gel of mesh size of 60-120 using 70:30 EtOAc:hexane as eluent) afforded 2-hydroxy-N-[2-Oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazine-1-yl]-ethyl]-benzamide in 25% yield. LC-MS purity: 97%, 1H NMR (DMSO-D6): δ 12.0 (s, 1H), 9.1 (t, 1H), 7.9 (m, 3H), 7.7 (d, 1H), 7.6 (m, 1H), 7.4 (t, 1H), 6.9 (t, 2H), 4.2 (dd, 2H), 3.6 (m, 4H), 3.4 (m, 2H), 3.2 (m, 2H).

Provenance & Evidence