di-tert-butyl (6-{[(4-phenyl-1-trityl-1H-imidazol-2-yl)(3-ethoxy-5-ethyl-2-fluorophenyl)methyl]amino}isoquinolin-1-yl)imidodicarbonate → HCID 178466284, compound
Reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH:31]([NH:44][C:45]3[CH:46]=[C:47]4[C:52](=[CH:53][CH:54]=3)[C:51]([N:55]([C:63]([O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:64])[C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])=[N:50][CH:49]=[CH:48]4)[C:32]3[CH:37]=[C:36]([CH2:38][CH3:39])[CH:35]=[C:34]([O:40][CH2:41][CH3:42])[C:33]=3[F:43])[N:10](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CC(O)=O>[C:1]1([C:7]2[N:8]=[C:9]([CH:31]([NH:44][C:45]3[CH:46]=[C:47]4[C:52](=[CH:53][CH:54]=3)[C:51]([N:55]([C:56]([O:58][C:59]([CH3:60])([CH3:61])[CH3:62])=[O:57])[C:63]([O:65][C:66]([CH3:67])([CH3:68])[CH3:69])=[O:64])=[N:50][CH:49]=[CH:48]4)[C:32]3[CH:37]=[C:36]([CH2:38][CH3:39])[CH:35]=[C:34]([O:40][CH2:41][CH3:42])[C:33]=3[F:43])[NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
3
Procedure
A solution of intermediate 448.4 (780 mg, 0.844 mmol) in 90% aq. AcOH was stirred at rt for 3.5 h, then concentrated. The residue was dissolved in EtOAc. The solution was washed with sat. NaHCO3, H2O and brine. The organic phase was dried (Na2SO4), then concentrated. The crude product was purified by flash chromatography (0 to 80% EtOAc/hexanes gradient) to afford 544 mg of intermediate 448.5 as a white solid. LCMS (2 min. gradient) RT=1.82 min, 682.56 (M+H)+.