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

HRID 23531Notes

Reaction equation

HRID 23531 reaction equation
C1(C2N[C:9]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([NH2:24])[CH:19]=3)=[C:10]([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)N=2)C=CC=CC=1.N([O-])=O.[Na+].[C:29]([O-:32])(O)=[O:30].[Na+].[OH2:34]>>[O:34]=[C:10]([C:12]1[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=1)[CH2:9][C:18]1[CH:23]=[CH:22][N:21]=[C:20]([NH:24][C:29](=[O:30])[O:32][C:12]([CH3:17])([CH3:13])[CH3:10])[CH:19]=1

Participants

5

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 23668193Sodium Nitrite2×HCID 178507343HCID 178507343, compound

Product 1

HCID 22574132Tert-butyl 4-[2-oxo-2-(4-pyridinyl)ethyl]-2-pyridinylcarbamateYield 31%

Procedure

The 4-[2-phenyl-4-(4-pyridinyl)-1H-imidazol-5-yl]-2-pyridinamine (86 mg, 0.27 mmol) was dissolved in 1.5 mL water containing 0.1 mL conc. Sulfuric acid and was treated with NaNO2 (24 mg, 0.38 mmol) and stirred 60 minutes. Another 7 mg NaNO2 (0.01 mmol) was added and the reaction was heated over a steam bath for 5 min. then was cooled to r.t. The reaction was basified with sat. NaHCO3 and was extracted with ethyl acetate. The combined organics were dried over Na2SO4, filtered and concentrated under reduced pressure to give a pale yellow solid which was triturated in ether to give 27 mg (31%) of the title compound as a pale yellow solid.

Workup

  1. temperaturethe reaction was heated over a steam bath for 5 min.
  2. extractionwas extracted with ethyl acetate
  3. dry with materialThe combined organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give a pale yellow solid which
  7. customwas triturated in ether

Sources & evidence

ORD record
ord-c90a8386a3b64ffb999a6d47e1b594dc
Source dataset
uspto-grants-2005_02
Patent number
US06852727B2

Reaction notes

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