Hydrochloric Acid → HCID 86646552, compound

Reaction equation

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]=1

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 887Methanol

HCID 7043Veratrole

HCID 86646553HCID 86646553, compound

Product 1

HCID 86646552HCID 86646552, compound

Procedure

To 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.