Aniline → HCID 9982385, compound

Participants

Reaction Steps

To 40 mg (0.10 mmol) of acid 24-1 in DMF was added 11 μL (0.12 mmol) of aniline, 29 mg (0.15 mmol) of EDCI, 17 mg (0.13 mmol) HOAT, and 28 μL (0.20 mmol) of triethylamine. After stirring overnight at room temperature, the reaction was partitioned between EtOAc and 10% KHSO4, the organic phase was washed with saturated NaHCO3, brine, dried over MgSO4, and concentrated. The residue was purified by column chromatography on silica gel with EtOAc/hexanes to provide 24-2 as a white solid. Data for 24-2: 1HNMR (500 MHz, d6-DMSO) δ 9.8 (s, 1H), 7.5-7.0 (m, 13H), 6.2 (s, 1H), 5.0 (m, 1H), 4.8 (m, 1H), 3.0 (m, 1H), 2.75 (s, 6H), [(˜2.5, under solvent peak (m, 1H)], 2.2 (m, 2H) ppm. HRMS (ES) calc'd M+H for C28H27F2N3O2: 476.2144. Found: 476.2162

Provenance & Evidence