CC1C=C(C=CC=1C(F)(F)F)[C:5]([NH:7][C:8]1[CH:9]=[N:10][C:11]([O:14][C:15]2[CH:23]=[C:22]3[C:18]([CH:19]=[C:20]([C:27]([N:29]4[CH2:34][CH2:33][N:32]([CH2:35][C:36]5[CH:41]=[CH:40][C:39]([O:42][CH2:43][C:44]([F:47])([F:46])[F:45])=[CH:38][CH:37]=5)[CH2:31][CH2:30]4)=[O:28])[N:21]3COC)=[CH:17][CH:16]=2)=[CH:12][CH:13]=1)=O.[C:55]1(OC)[C:56](=[CH:59][CH:60]=[CH:61][CH:62]=1)OC.Cl.[CH3:66][OH:67]>>[CH3:5][N:7]([C:8]1[CH:9]=[N:10][C:11]([O:14][C:15]2[CH:23]=[C:22]3[C:18]([CH:19]=[C:20]([C:27]([N:29]4[CH2:30][CH2:31][N:32]([CH2:35][C:36]5[CH:37]=[CH:38][C:39]([O:42][CH2:43][C:44]([F:46])([F:45])[F:47])=[CH:40][CH:41]=5)[CH2:33][CH2:34]4)=[O:28])[NH:21]3)=[CH:17][CH:16]=2)=[CH:12][CH:13]=1)[C:66](=[O:67])[C:61]1[CH:62]=[CH:55][C:56]([C:44]([F:47])([F:46])[F:45])=[CH:59][CH:60]=1To a solution of M-methyl-N-[6-(1-methoxymethyl-2-{4-[4-(2,2,2-trifluoroethoxy)benzyl]piperazine-1-carbonyl}-1H-indol-6-yloxy)pyridin-3-yl]-4-trifluoromethylbenzamide (0.24 g, 0.31 mmol) in MeOH (12 mL) were added veratrole (0.43 g, 3.1 mmol) and 2 M HCl (6 mL), and the mixture was stirred under reflux for 7 hours. The solvent was evaporated in vacuo, and the residue was extracted with AcOEt. The organic layer was washed with saturated aqueous NaHCO3 and brine, dried over anhydrous sodium sulfate and evaporated. The residue was purified by silica gel column chromatography (AcOEt) to give 0.34 g of the title compound as a colorless powder.
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