Sodium Chloride → HCID 67363169, compound

HRID 245703Notes

Reaction equation

HRID 245703 reaction equation
Cl.[CH3:2][C:3]1[C:4]2[N:5]([C:9]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)=[N:10][CH:11]=2)[CH:6]=[CH:7][N:8]=1.C(N(CC)CC)C.[C:25](OC(=O)C)(=[O:27])[CH3:26].C(=O)([O-])O.[Na+].[Cl-].[Na+]>ClCCl>[CH3:2][C:3]1[C:4]2[N:5]([C:9]([N:12]3[CH2:17][CH2:16][N:15]([C:25](=[O:27])[CH3:26])[CH2:14][CH2:13]3)=[N:10][CH:11]=2)[CH:6]=[CH:7][N:8]=1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 67365154HCID 67365154, compound

Product 1

HCID 67363169HCID 67363169, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 8-methyl-3-(piperazin-1-yl)imidazo[1,5-a]pyrazine hydrochloride (0.359 mmol, 91 mg) and triethylamine (1.793 mmol, 0.250 ml) in dichloromethane (5 ml) was added acetic anhydride (0.538 mmol, 0.051 ml). After stirring at room temperature for 20 hours saturated aqueous sodium hydrogencarbonate solution was added and the mixture extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried (sodium sulfate), and concentrated in vacuo to give 24 mg of crude product. To the aqueous layer solid sodium chloride was added and the mixture extracted three times with dichloromethane/methanol (4/1). The combined organic layers were washed with brine, dried (sodium sulfate), and concentrated in vacuo to give an additional 47 mg of crude product. The combined crude samples were purified using column chromatography (silica gel; dichloromethane with gradient 0 to 10% methanol) to give 1-(4-(8-methylimidazo[1,5-a]pyrazin-3-yl)piperazin-1-yl)ethanone (56 mg).

Workup

  1. additionwas added
  2. extractionthe mixture extracted three times with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. customto give 24 mg of crude product
  7. extractionthe mixture extracted three times with dichloromethane/methanol (4/1)
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried (sodium sulfate)
  10. concentrationconcentrated in vacuo
  11. customto give an additional 47 mg of crude product
  12. customThe combined crude samples were purified

Sources & evidence

ORD record
ord-220b75e10ee14b5086fabde1f1180ed8
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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