Acetyl chloride → 1-(2-Nitro-6,7-dihydropyrazolo[1,5-a]pyrazin-5(4H)-yl)ethanone

HRID 407686Notes

Reaction equation

HRID 407686 reaction equation
[N+:1]([C:4]1[CH:12]=[C:7]2[CH2:8][NH:9][CH2:10][CH2:11][N:6]2[N:5]=1)([O-:3])=[O:2].[C:13](Cl)(=[O:15])[CH3:14].C([O-])([O-])=O.[K+].[K+]>ClCCl>[N+:1]([C:4]1[CH:12]=[C:7]2[CH2:8][N:9]([C:13](=[O:15])[CH3:14])[CH2:10][CH2:11][N:6]2[N:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 580442792-Nitro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine

Product 1

HCID 580439581-(2-Nitro-6,7-dihydropyrazolo[1,5-a]pyrazin-5(4H)-yl)ethanoneYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 124d (672 mg, 4.0 mmol) in dichloromethane (20 mL) was added acetyl chloride (936 mg, 12.0 mmol) and K2CO3 (1104 mg, 8.0 mmol). The mixture was stirred overnight. It was then filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica-gel column chromatography eluting with 100:1 dichloromethane/methanol to afford 124e as white solid (500 mg, 60%). MS: [M+H]+ 211.2

Workup

  1. filtrationIt was then filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe resulting residue was purified by silica-gel column chromatography
  4. washeluting with 100:1 dichloromethane/methanol

Sources & evidence

ORD record
ord-84f9d8c3a6e5449083793164d3b9736d
Source dataset
uspto-grants-2014_06
Patent number
US08754077B2

Reaction notes

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