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

HRID 1185100Notes

Reaction equation

HRID 1185100 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-bbf01be2d6f24953b872efebcec91baa
Source dataset
uspto-grants-2014_03
Patent number
US08669251B2

Reaction notes

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