Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[CH:9]2)=[CH:4][CH:3]=1.[C:12]([O-])(O)=O.[Na+].C(OC([NH:24][CH2:25][CH2:26][NH2:27])=O)(C)(C)C.N1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[SH:34]([O:37]Cl)(=O)=[O:35]>C(Cl)Cl>[NH2:27][CH2:26][CH2:25][NH:24][S:34]([C:4]1[C:5]2[CH:6]=[CH:7][N:8]=[CH:9][C:10]=2[CH:11]=[C:2]([C:29]2[CH:12]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:3]=1)(=[O:37])=[O:35]A mixture of 7-bromoisoquinoline (6.5 g, 31.24 mmol) in HSO3Cl (60 mL) is heated to 155° C. with stirring under N2 overnight, and then cooled to room temperature and slowly poured into ice water. After neutralizing with NaHCO3 at 0° C., sulfonyl chloride is extracted with methylene chloride. The organic layer is dried over Na2SO4 and concentrated to 100 mL and dropped to a solution of N-t-butoxycarbonylethylene diamine (5.01 g, 31.24 mmol) in pyridine (2.54 mL, 31.24 mmol) and CH2Cl2 (120 mL). After stirring overnight, the mixture is concentrated, and the residue is dissolved in EtOAc, which is washed with citric acid solution (50%) and brine. The crude material is purified by chromatography over silica gel (gradient 20% hexane in EtOAc) to give 6.50 g (50% yield) of desired product
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