Hydrochloric Acid → methyl 3-cyclohexyl-2-{4-methoxy-2-[(methylamino)methyl]phenyl}-1-(2-oxoethyl)-1H-indole-6-carboxylate
Reaction equation
Cl.[CH:2]1([C:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][CH:15]=3)[N:10]([CH2:21][CH:22]3OCC[O:23]3)[C:9]=2[C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=2[CH2:35][NH:36][CH3:37])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1>C1COCC1>[CH:2]1([C:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][CH:15]=3)[N:10]([CH2:21][CH:22]=[O:23])[C:9]=2[C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=2[CH2:35][NH:36][CH3:37])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1Participants
4
Procedure
Aqueous HCl (25 eq, 3 M) was added to a solution of methyl 3-cyclohexyl-1-(1,3-dioxolan-2-ylmethyl)-2-{4-methoxy-2-[(methylamino)methyl]phenyl}-1H-indole-6-carboxylate in THF (0.02 M), and the mixture heated at reflux for 24 h. The volatiles were reduced in vacuo, and the residue partitioned between EtOAc and saturated aqueous NaHCO3 (ensuring that the aqueous phase is basic). The aqueous phase was extracted with EtOAc and the combined organics washed with water and brine, before being dried (Na2SO4), filtered and concentrated in vacuo to give the title compound in essentially quantitative yield; MS (ES+) m/z 449 (M+H)+.