HCID 23070798, compound → HCID 23070760, compound

HRID 501449Notes

Reaction equation

HRID 501449 reaction equation
[CH2:1]([N:5]1[C:9]([C:10]#[N:11])=[C:8]([CH2:12][OH:13])[N:7]=[C:6]1[N:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)[C:2]#[C:3][CH3:4]>[O-2].[O-2].[Mn+4].ClCCl>[CH2:1]([N:5]1[C:9]([C:10]#[N:11])=[C:8]([CH:12]=[O:13])[N:7]=[C:6]1[N:14]1[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]1)[C:2]#[C:3][CH3:4]

Participants

4

Reactant 1

HCID 23070798HCID 23070798, compound

Product 1

HCID 23070760HCID 23070760, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

3.28 g of manganese dioxide was added to a 5 ml dichloromethane solution of 1.35 g of t-butyl 4-[1-(2-butynyl)-5-cyano-4-hydroxymethyl-1H-imidazol-2-yl]piperazine-1-carboxylate. The reaction solution was stirred at room temperature for 15 hours, then stirred and heated under reflux for five hours. The solution was filtered, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 1.11 g of the title compound was obtained from the fraction eluted with ethyl acetate-hexane (2:3).

Workup

  1. stirringstirred
  2. temperatureheated
  3. temperatureunder reflux for five hours
  4. filtrationThe solution was filtered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-805f23e9a49c48e58520f266903c0756
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

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