Trifluoroacetic acid → Tert-butyl 4-[2-oxo-2-(4-pyridinyl)ethyl]-2-pyridinylcarbamate

HRID 23530Notes

Reaction equation

HRID 23530 reaction equation
FC(F)(F)C(O)=[O:4].C1(C2[NH:15][C:16]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH:26]=3)=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)N=2)C=CC=CC=1>ClCCl>[NH4+:15].[OH-:4].[O:4]=[C:17]([C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1)[CH2:16][C:25]1[CH:30]=[CH:29][N:28]=[C:27]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH:26]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178452644HCID 178452644, compound

Product 2

HCID 14923Ammonium HydroxideHCID 22574132Tert-butyl 4-[2-oxo-2-(4-pyridinyl)ethyl]-2-pyridinylcarbamateYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (8 mL) was added to tert-butyl 4-[2-phenyl-4-(4-pyridinyl)-1H-imidazol-5-yl]-2-pyridinylcarbamate in dichloromethane (10 mL) and after 42 h, the volatiles were removed under reduced pressure. The residue was diluted with ethyl acetate and was washed with st. K2CO3, dried over Na2SO4, filtered and concentrated in vacuo to give a yellow solid which was purified by silica gel chromatography, eluting with 95 CH2Cl2:5 CH3OH:0.5 NH4OH to afford the 258 mg (50%) of the titled compound as a yellow solid. Step D: 4-(2-phenyl-4-pyridin-4-yl-1H-imidazol-5-yl)pyridin-2(1H)-one

Workup

  1. customthe volatiles were removed under reduced pressure
  2. additionThe residue was diluted with ethyl acetate
  3. washwas washed with st
  4. dry with materialK2CO3, dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a yellow solid which
  8. customwas purified by silica gel chromatography
  9. washeluting with 95 CH2Cl2

Sources & evidence

ORD record
ord-4a48228f49e0452baa2414d569a2f24c
Source dataset
uspto-grants-2005_02
Patent number
US06852727B2

Reaction notes

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