[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][C:9]2[CH:22]=[CH:21][C:12]3[N:13]=[C:14]([NH:16][C:17](=[O:20])[O:18][CH3:19])[S:15][C:11]=3[CH:10]=2)=[CH:6][CH:5]=1)([O-])=O.Cl[Sn]Cl>CN(C=O)C>[NH2:1][C:4]1[CH:24]=[CH:23][C:7]([O:8][C:9]2[CH:22]=[CH:21][C:12]3[N:13]=[C:14]([NH:16][C:17](=[O:20])[O:18][CH3:19])[S:15][C:11]=3[CH:10]=2)=[CH:6][CH:5]=1To a solution of methyl (6-(4-nitrophenoxy)benzthiazole-2-yl)carbamate (Intermediate 10E-172.7 mg, 0.5 mmol) in DMF (5 mL) was added SnCl2 (474.0 mg, 2.5 mmol) and stirred at room temperature for 4 days. The mixture was extracted with ethyl acetate, and the organic layer was washed with NaHCO3aq. and dried over Na2SO4 then evaporated to remove solvent. The residue dissolved in small amount of DMF was charged on SCX column chromatography then washed with MeOH then eluted with NH3—MeOH to give the title compound (69.2 mg, 44%): MS m/e 316 (M+1).
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