反应详情

In a round bottom flask under nitrogen was combined 4-{4-[2-(4-tert-Butyl-phenyl)-1H-benzoimidazol-4-yl]-piperazin-1-ylmethyl}-benzene-1,2-diamine (0.17 g, 0.37 mMol), tetrahydrofuran (20 mL), and 1,1′-oxalyldiimidazole (0.284 g, 1.5 mMol) and the solution stirred overnight. Upon arrival the solution was diluted with ethyl acetate (100 mL) and washed with water (100 mL). A precipitate forms and was collected by filtration. The organic layer was concentrated to dryness on a rotary evaporator and combined with the precipitate. Purification by RP-HPLC (Method E) yielded 46 mg (24% yield) of 6-{4-[2-(4-tert-Butyl-phenyl)-1H-benzoimidazol-4-yl]-piperazin-1-ylmethyl}-1,4-dihydro-quinoxaline-2,3-dione as an off-white solid. 1H NMR (DMSO-d6): δ=12.19 (s, 1H), 12.09 (s, 1H), 9.82 (br s, 1H), 8.07 (d, 2H, J=8.6 Hz), 7.58 (d, 2H, J=8.6 Hz), 7.27 (m, 2H), 7.22 (d ,1H, J=8.6 Hz), 7.13 (m, 2H), 6.64 (m, 1H), 4.48 (br s, 2H), 4.44 (s, 2H), 3.50 (br s, 2H), 3.38 (br s, 2H), 3.09 (m, 2H), 1.34 (s, 9H). HPLC: Xterra MS C18, 3.5 μm, 4.6×50 mm, flow=0.8 m/min, 5-95% ACN/PICB6 over 10 mins., rt=5.840 mins., 79% pure @ 210 nm, 77% pure @ 300 nm. LC/MS (Method A), rt=1.05 mins., purity=79.19%, calculated mass=508, [M+H]+=509, [M−H]−=507.

1. customIn a round bottom flask under nitrogen was combined
2. washwashed with water (100 mL)
3. filtrationA precipitate forms and was collected by filtration
4. concentrationThe organic layer was concentrated to dryness on a rotary evaporator
5. customPurification by RP-HPLC (Method E)