2-Methylbenzoic acid → HCID 25165913, compound

Participants

Reaction Steps

DIPEA (152 mg, 0.66 mmol) was added to a stirred solution of biphenyl-4-carboxylic acid (2-oxo-2-piperazin-1-yl-ethyl)-amide TFA salt (116 mg, 0.26 mmol) in DMF (1 mL). HOBT (36 mg, 0.26 mmol) and EDCI.HCl (50 mg, 0.26 mmol) were then added. After 2 minutes 2-methylbenzoic acid (30 mg, 0.22 mmol) was added and the resulting mixture was stirred overnight. The reaction mixture was diluted with cold water. The product was extracted with ethyl acetate and the ethyl acetate layer was washed with NaHCO3 solution, saturated brine solution, dried over sodium sulphate and concentrated under reduced pressure. The residue was washed with diethyl ether to afford 62 mg (72.9% yield) of biphenyl-4-carboxylicacid {2-[4-(2-methyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-amide as a pale yellow solid. LC-MS purity: 94.42%, HPLC Purity: 92.84%. 1H NMR: (DMSO) δ 8.7-8.6 (bs, 1H), 8.0 (d, 2H) 7.8 (m, 4H), 7.6-7.2 (m, 7H), 4.1-4.3 (dd, 2H), 3.8-3.4 (m, 6H), 3.2 (m, 2H), 2.2 (s, 3H).

Provenance & Evidence