Ethyl Acetate → HCID 57642838, compound

HRID 2112924Notes

Reaction equation

HRID 2112924 reaction equation
C(=O)(O)[O-].[Na+].[Br:6]N1C(=O)CCC1=O.[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][N:24]([C:27]2[C:32]3[N:33]([CH2:38][C:39]#[C:40][CH3:41])[C:34](=[O:37])[N:35]([CH3:36])[C:31]=3[CH:30]=[CH:29][N:28]=2)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].C(OCC)(=O)C>CN(C)C=O.O>[C:14]([O:18][C:19]([N:21]1[CH2:22][CH2:23][N:24]([C:27]2[C:32]3[N:33]([CH2:38][C:39]#[C:40][CH3:41])[C:34](=[O:37])[N:35]([CH3:36])[C:31]=3[C:30]([Br:6])=[CH:29][N:28]=2)[CH2:25][CH2:26]1)=[O:20])([CH3:17])([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimide2×HCID 516892Sodium Bicarbonate2×HCID 57642836HCID 57642836, compound

Product 1

HCID 57642838HCID 57642838, compoundYield 37.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium bicarbonate (0.146 g) and N-bromosuccinimide (0.288 g) were added to a solution of 4-[3-(2-butynyl)-1-methyl-2-oxo-2,3-dihydro-1H-imidazo[4.5-c]pyridin-4-yl]-piperazine-1-carboxylic acid t-butyl ester (0.447 g) in N,N-dimethylformamide (20 mL). This was then stirred at room temperature for 60 hours. Sodium bicarbonate (0.219 g) and N-bromosuccinimide (0.432 g) were added again, and this was stirred at room temperature for 15 hours. Ethyl acetate (100 mL) and water (50 mL) were then added, and the organic layer was washed twice with 50 mL of water and then once with 50 mL of saturated aqueous sodium chloride solution, then was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography, and the hexane:ethyl acetate 1:1 fraction gave the title compound (0.201 g).

Workup

  1. stirringthis was stirred at room temperature for 15 hours
  2. washthe organic layer was washed twice with 50 mL of water
  3. dry with materialonce with 50 mL of saturated aqueous sodium chloride solution, then was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-9b2b93c67d83481b8a7f55d87937cf1a
Source dataset
uspto-grants-2009_04
Patent number
US07524847B2

Reaction notes

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