Acetic Anhydride → HCID 25184842, compound

HRID 1878071Notes

Reaction equation

HRID 1878071 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10]O)=[NH:9])=[N:6][CH:7]=1.[C:12]([O:15][C:16](=[O:18])[CH3:17])(=[O:14])[CH3:13].[H][H]>C(O)(=O)C.[Pd]>[C:12]([OH:15])(=[O:14])[CH3:13].[C:8]([C:5]1[N:6]=[CH:7][C:2]([NH:1][C:16](=[O:18])[CH3:17])=[CH:3][CH:4]=1)(=[NH:9])[NH2:10]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 178418361HCID 178418361, compoundHCID 178513343HCID 178513343, compound

Product 1

HCID 25184842HCID 25184842, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of compound of example 1 (0.2 g, 1.32 mmol) in acetic acid was added acetic anhydride (0.202 g, 1.98 mmol) and the reaction mixture was stirred at a temperature of 25° C. for 5 minutes. To the reaction mixture, 10% Pd/C (0.028 g) was added and shaken with hydrogen on Parr hydrogenation apparatus at a pressure of about 15 psi for a period of 4 hours. The reaction mixture was filtered through celite and the filter pad was washed with glacial acetic acid (15 mL). The filtrate was combined and acid removed under reduced pressure. The traces of acid were removed by using petroleum ether and the solid obtained was purified by column chromatography using silica gel and 10% methanol/chloroform as eluent to obtain the title compound.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washthe filter pad was washed with glacial acetic acid (15 mL)
  3. customacid removed under reduced pressure
  4. customThe traces of acid were removed
  5. customthe solid obtained
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-5b20e96a66b94f26a6a109f62467b5ea
Source dataset
uspto-grants-2012_11
Patent number
US08314103B2

Reaction notes

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