[Si](Br)(C)(C)C.CS(C)=O.[C:10]1([CH2:16][CH:17]=O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[N:19]1([CH2:24][CH2:25][O:26][C:27]2[CH:32]=[CH:31][C:30]([NH:33][C:34]([NH2:36])=[S:35])=[CH:29][CH:28]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1>CC#N>[C:10]1([C:16]2[S:35][C:34]([NH:33][C:30]3[CH:31]=[CH:32][C:27]([O:26][CH2:25][CH2:24][N:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)=[CH:28][CH:29]=3)=[N:36][CH:17]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1Me3SiBr (0.052 mL, 0.384 mmol, 1.1 equiv) and DMSO (0.027 mL, 0.384 mmol, 1.1 equiv) are added sequentially and dropwise to a cold (0° C.) solution of phenylacetaldehyde (42 mg, 0.349 mmol) in CH3CN (0.66 mL), under an argon atmosphere. The resulting mixture is stirred at 0° C. for 50 min, allowed to warm to RT and to stir for 10 min. CH3CN (0.97 mL) is added to the reaction mixture, followed by addition of [4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-thiourea (93 mg, 0.349 mmol). The reaction mixture is heated to reflux for 80 min, allowed to cool to RT and concentrated in vacuo. Purification of the crude product by silica gel (20 g) column chromatography (CH2Cl2/MeOH, 90/10) affords the title compound: ES-MS: 366.0 [M+H]+; single peak at tR=6.33 min (System 1); Rf=0.11 (CH2Cl2/MeOH, 80/20).
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