Acetic Anhydride → 1-(4-{3-[7-(1-Methyl-cyclohexanecarbonyl)-5h-pyrrolo[2,3-b]pyrazin-2-yl]-phenyl}-piperazin-1-yl)-ethanone

HRID 1677481Notes

Reaction equation

HRID 1677481 reaction equation
[CH3:1][C:2]1([C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([N:25]5[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]5)[CH:20]=4)[N:17]=3)[NH:12][CH:11]=2)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[C:31](OC(=O)C)(=[O:33])[CH3:32].[OH-].[Na+]>CN(C=O)C.C1COCC1>[CH3:1][C:2]1([C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:19]4[CH:20]=[C:21]([N:25]5[CH2:30][CH2:29][N:28]([C:31](=[O:33])[CH3:32])[CH2:27][CH2:26]5)[CH:22]=[CH:23][CH:24]=4)[N:17]=3)[NH:12][CH:11]=2)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 59540704(1-methyl-cyclohexyl)-[2-(3-piperazin-1-yl-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone

Product 1

HCID 595409231-(4-{3-[7-(1-Methyl-cyclohexanecarbonyl)-5h-pyrrolo[2,3-b]pyrazin-2-yl]-phenyl}-piperazin-1-yl)-ethanone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 0° C. solution of (1-methyl-cyclohexyl)-[2-(3-piperazin-1-yl-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone (24 mg, 0.06 mmol) in DMF (1 ml) was treated with Acetic anhydride (0.01 ml, 0.06 mmol). The reaction mixture was removed from the ice bath and allowed to stir at room temperature for 16 hours. The reaction mixture was partitioned between EtOAc/sat. NaHCO3. The organic layers were collected, dried over MgSO4, filtered, and concentrated giving a white solid which was filtered through a Buchner funnel and washed with Et2O and Hexanes to afford a yellow solid. The yellow solid was dissolved in THF (2 ml) and treated with 1N NaOH (0.05 ml, 0.05 mmol). After stirring at room temperature for 16 hours, the reaction mixture was partitioned between 1N HCl and EtOAc. The organic layers were collected, dried over MgSO4, filtered, and concentrated giving a light brown oil. The oil was triturated with Et2O providing 4 mg (15%) of 1-(4-{3-[7-(1-methyl-cyclohexanecarbonyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-phenyl}-piperazin-1-yl)-ethanone as a pale brown solid. M+H=446.

Workup

  1. customThe reaction mixture was removed from the ice bath
  2. customThe reaction mixture was partitioned between EtOAc/
  3. customThe organic layers were collected
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customgiving a white solid which
  8. filtrationwas filtered through a Buchner funnel
  9. washwashed with Et2O and Hexanes
  10. customto afford a yellow solid
  11. stirringAfter stirring at room temperature for 16 hours
  12. customthe reaction mixture was partitioned between 1N HCl and EtOAc
  13. customThe organic layers were collected
  14. dry with materialdried over MgSO4
  15. filtrationfiltered
  16. concentrationconcentrated
  17. customgiving a light brown oil
  18. customThe oil was triturated with Et2O providing 4 mg (15%) of 1-(4-{3-[7-(1-methyl-cyclohexanecarbonyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-phenyl}-piperazin-1-yl)-ethanone as a pale brown solid

Sources & evidence

ORD record
ord-156f5cec66284966ad1dec32dfd81018
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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