[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=O)[CH2:7][CH2:6]2.[CH2:14](N)[CH2:15][NH2:16].CC1C=CC(S(O)(=O)=O)=CC=1.O.Cl.[OH-].[Na+]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]1[CH2:14][CH2:15][N:16]=[C:8]1[CH2:7][CH2:6]2To a mixture of Compound 13 (0.50 g, 2.6 mmol) and ethylenediamine (0.88 ml, 13.1 mmol) was added p-TsOH.H2O (2.5 g, 13.1 mmol), and heated to 200° C. for 24 h. The cooled mixture was solved with 6N HCl, basified with NaOH aq., and extracted with CH2Cl2. The organic layers were combined, dried over MgSO4, filtered, and concentrated. This residue was purified by SiO2 chromatography to give Compound 14 (63 mg, 0.31 mmol, 12%) as a colorless oil.
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