Acetic Anhydride → HCID 11993090, compound

HRID 421838Notes

Reaction equation

HRID 421838 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH2:8][C:9](=[N:30]O)[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([N:16]2[CH2:21][CH2:20][N:19]([C:22](=[O:29])[CH2:23][CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:18][CH2:17]2)[CH:11]=1>>[CH3:26][C:25]([CH3:28])([CH3:27])[CH2:24][CH2:23][C:22]([N:19]1[CH2:20][CH2:21][N:16]([C:12]2[CH:11]=[C:10]([C:9]3[N:30]=[C:5]([CH3:6])[O:7][N:8]=3)[CH:15]=[CH:14][N:13]=2)[CH2:17][CH2:18]1)=[O:29]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 136381719HCID 136381719, compound

Product 1

HCID 11993090HCID 11993090, compound

Procedure

Acetic anhydride (2 mL) was added to 1-{4-[amino(hydroxyimino)methyl]pyridin-2-yl}-4-(4,4-dimethylpentanoyl)piperazine (104 mg) obtained in Example 56-1), heated under reflux for 2 hours, then the excess acetic anhydride was evaporated away, the residue was diluted with ethyl acetate, washed with aqueous saturated sodium hydrogencarbonate solution and saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated away, and the resulting residue was isolated and purified through thin-layer silica gel chromatography (hexane/ethyl acetate=1/1) to obtain 14.5 mg of the entitled compound as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. customthe excess acetic anhydride was evaporated away
  4. additionthe residue was diluted with ethyl acetate
  5. washwashed with aqueous saturated sodium hydrogencarbonate solution and saturated saline water
  6. dry with materialdried with anhydrous sodium sulfate
  7. customThe solvent was evaporated away
  8. customthe resulting residue was isolated
  9. custompurified through thin-layer silica gel chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-a22a66038a544ac3b5cc318e579c9fb7
Source dataset
uspto-grants-2012_01
Patent number
US08101618B2

Reaction notes

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