Cl.Cl.[NH2:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([NH2:9])=N.C[N:14](C=O)C.[C:18]1(=[O:25])[O:24][C:22](=[O:23])[CH2:21][CH2:20][CH2:19]1>CN(C1C=CC=CN=1)C.N1C=CC=CC=1>[NH2:14][N:9]=[CH:7][C:6]1[CH:5]=[C:4]([NH:3][CH:21]([CH:22]=[O:23])[CH2:20][CH2:19][C:18]([OH:24])=[O:25])[CH:12]=[CH:11][CH:10]=13-Aminobenzamidine di-HCL (5 g, 24 mmol) was added to dry DMF (30 mL). To this solution dry pyridine (5 mL) and glutaric anhydride (3.0 g, 26 mmol), followed by 10 mg dimethylaminopyridine (DMAP) were added. The product was heated for 3 h at 100° C. and allowed to stir at room temperature for 16 h. Solvents were removed in vacuo, water was added to the residue and the pH was brought to a value of 6.8 using dilute sodium hydroxide. An abundant precipitate was filtered, washed with water followed by ethyl acetate. The white solid was filtered and dried in a desiccator to give 5.4 g, 90% of product as a white solid: 1H NMR (d6 -DMSO) δ 1.8 (m, 2H), 2.3 (m, 2H), 2.45 (m, 2H), 7.6 (d, 1H, J=8 Hz), 7.55 (dd, 1H, J=8 Hz and J= 7.5 Hz), 7.85 (d, 1H, J=7.5 Hz), 8.05 (s, 1H), 9.05 (bs, 2H), 9.25 (bs, 2H), 10.4 (s, 1H); MS (FAB) m/e 250.1 (MH+).
Loading…
