I([O-])(=O)(=O)=O.[Na+].[N:7]1([CH2:12][CH2:13][C:14]2[S:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[C:15]=2[C:23]([C:25]2[N:26]=[CH:27][S:28][CH:29]=2)=[CH2:24])[CH2:11][CH2:10][CH2:9][CH2:8]1.NN.N>O.CCO>[N:7]1([CH2:12][CH2:13][C:14]2[S:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[C:15]=2[CH:23]([C:25]2[N:26]=[CH:27][S:28][CH:29]=2)[CH3:24])[CH2:8][CH2:9][CH2:10][CH2:11]1To a mixture of EtOH (7 mL) and water (2 mL), sodium periodate (1.4 g, 6.62 mmol), 4-{1-[2-(2-pyrrolidin-1-yl-ethyl)-benzo[b]thiophen-3-yl]-vinyl}-thiazole (225 mg, 0.66 mmol) and hydrazine (880 uL, 27 mmol) were added. The reaction was refluxed for 90 min, cooled down to room temperature and additional hydrazine (880 uL, 27 mmol) and sodium periodate (1.4 g, 6.6 mmol) were added. The reaction was refluxed for an additional hour, cooled down and additional aliquots of hydrazine (880 uL, 27 mmol) and sodium periodate (1.4 g, 6.6 mmol) were added. After refluxing overnight, water and ammonia were added (pH ˜9), which was followed by extraction with EtOAc, drying (MgSO4), filtration, and concentration in vacuo. Mass triggered preparative HPLC afforded 4-{1-[2-(2-pyrrolidin-1-yl-ethyl)-benzo[b]thiophen-3-yl]-ethyl}-thiazole (Compound 19-4). MH+=343.
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