Ethyl Acetate → HCID 57642829, compound

HRID 2112916Notes

Reaction equation

HRID 2112916 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]([CH2:46][C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[C:34](=[O:45])[N:35]([CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=4[C:43]#[N:44])[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>C(#N)C.O>[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][N:24]([C:27]2[C:32]3[N:33]([CH2:46][C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[C:34](=[O:45])[N:35]([CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=4[C:43]#[N:44])[C:31]=3[C:30]([Br:6])=[CH:29][N:28]=2)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:15])[CH3:16]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 57642820HCID 57642820, compound

Product 1

HCID 57642829HCID 57642829, compoundYield 106.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Sodium bicarbonate (0.029 g) and N-bromosuccinimide (0.044 g) were added to a solution of 4-[3-benzyl-1-(2-cyanobenzyl)-2-oxo-1H-imidazo[4.5-c]pyridin-4-yl]-piperazine-1-carboxylic acid t-butyl ester (0.121 g) in acetonitrile (5 mL). This was then stirred at room temperature for 15 hours. Ethyl acetate (100 mL) and water (50 mL) were added, and the organic layer was dried over anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue was purified by silica gel chromatography, and the hexane:ethyl acetate 7:3 fraction gave the title compound (0.148 g).

Workup

  1. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-159586de449c4b0e83a2bb778fbd493f
Source dataset
uspto-grants-2009_04
Patent number
US07524847B2

Reaction notes

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