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

HRID 2105091Notes

Reaction equation

HRID 2105091 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]=1

Participants

3

Reactant 1

HCID 86607947di-tert-butyl (6-{[(4-phenyl-1-trityl-1H-imidazol-2-yl)(3-ethoxy-5-ethyl-2-fluorophenyl)methyl]amino}isoquinolin-1-yl)imidodicarbonate

Product 1

HCID 178466284HCID 178466284, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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)+.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in EtOAc
  3. washThe solution was washed with sat. NaHCO3, H2O and brine
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography (0 to 80% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-0c0fa61ef7664a43a1965472c1539fc4
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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