CCN(C(C)C)C(C)C.O[C:11]1[CH:12]=[C:13]([CH:21]=[CH:22][CH:23]=1)[C:14]([NH:16]CC(O)=O)=[O:15].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.N1(C(C2C=CC=CC=2C(F)(F)F)=O)CCNCC1>CN(C=O)C.O>[C:14]([NH2:16])(=[O:15])[C:13]1[CH:21]=[CH:22][CH:23]=[CH:11][CH:12]=1DIPEA (0.7692 g, 3 mmol) was added dropwise to (3-hydroxy-benzoyl amino)-acetic acid (50 mg, 0.26 mmol) in DMF (4 mL). EDCI (122 mg, 0.64 mmol) and HOBT (41 mg, 0.31 mmol) were added consecutively and after 10 mins, piperazin-1-yl-(2-trifluoromethyl-phenyl)-methanone (90 mg, 0.31 mmol) was added and was allowed to stir at room temperature overnight. 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 90:10 EtOAc:hexane as eluent) afforded 3-hydroxy-N-[2-Oxo-2-trifluoromethyl-benzoyl)-piperazine-1-yl]-ethyl]-benzamide in 39% yield. LC-MS purity: 98%, H1—NMR (DMSO-D6): δ 9.6 (s, 1H), 8.4 (d, 1H), 7.8 (dd, 2H), 7.7 (d, 1H), 7.6 (t, 1H), 7.2 (d, 3H), 6.9 (d, 1H), 4.1 (dd, 2H), 3.6 (m, 4H), 3.4 (s, 2H), 3.2 (d, 2H).
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