[CH3:1][S:2](Cl)(=[O:4])=[O:3].N1C=CC=CC=1.[NH2:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][C:21]=1[S:22][C:23]1[S:24][CH:25]=[CH:26][N:27]=1)[C:18](=[O:28])[CH2:17][CH2:16]2.CCN(CC)CC>C(Cl)Cl.O>[CH3:1][S:2]([N:12]([S:2]([CH3:1])(=[O:4])=[O:3])[C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][C:21]=1[S:22][C:23]1[S:24][CH:25]=[CH:26][N:27]=1)[C:18](=[O:28])[CH2:17][CH2:16]2)(=[O:4])=[O:3]Methanesulfonyl chloride (710 μL, 9.15 mmol) and pyridine (740 μL, 9.15 mmol) were added to a solution of the aminoindanone from Step 8 in CH2Cl2 (5 mL). After stirring overnight at room temperature, Et3N (400 μL, 2.8 mmol) and methanesulfonyl chloride (220 μL, 2.8 mmol) were added. The mixture was stirred 4 h at room temperature. Water and CH2Cl2 were added, the aqueous phase was extracted with CH2Cl2 and the combined organic phase was washed with 0.1M aqueous citric acid, dried over MgSO4 and concentrated in vacuo. The crude residue was purified by flash chromatography on silica gel (20% EtOAc in CHCl2) to give 175 mg of the title compound.
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