Diethyl squarate → HCID 57461812, compound

HRID 1020380Notes

Reaction equation

HRID 1020380 reaction equation
C(O[C:4]1[C:5](=[O:12])[C:6](=[O:11])[C:7]=1[O:8][CH2:9][CH3:10])C.[N+:13]([C:16]1[CH:17]=[CH:18][C:19]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[N:20][CH:21]=1)([O-:15])=[O:14]>CN(C=O)C.C(O)C.CO>[CH2:9]([O:8][C:7]1[C:6](=[O:11])[C:5](=[O:12])[C:4]=1[N:25]1[CH2:26][CH2:27][N:22]([C:19]2[CH:18]=[CH:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:21][N:20]=2)[CH2:23][CH2:24]1)[CH3:10]

Participants

6

Reactant 2

HCID 123228Diethyl squarateHCID 29287991-(5-Nitropyridin-2-yl)piperazine

Product 1

HCID 57461812HCID 57461812, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×

Procedure

To 3,4-diethoxycyclobut-3-ene-1,2-dione (1.20 mL, 8.10 mmol) in anhydrous DMF (10.0 mL) at room temperature was added a solution of 1-(5-nitropyridin-2-yl)piperazine (B-8) (1.926 g, 9.26 mmol) in anhydrous DMF (14.0 mL). The reaction mixture was stirred at room temperature for 3 h, and then diluted with absolute ethanol (40 mL) and methanol (30 mL). The yellow precipitate formed was filtered and washed with methanol (25 mL). The alcoholic filtrate was discarded, and the solid residue was dissolved in methylene chloride. The solution obtained was concentrated to give 3-ethoxy-4-(4-(5-nitropyridin-2-yl)piperazin-1-yl)cyclobut-3-ene-1,2-dione (C-9) as a yellow solid (1.93 g, 72% yield). MS (M+1): m/e 333. Nota: The presence of 1 equivalent 2-fluoroaniline or 2,6-dichloroaniline in the reaction mixture does not affect the course of the reaction in those conditions.

Workup

  1. customThe yellow precipitate formed
  2. filtrationwas filtered
  3. washwashed with methanol (25 mL)
  4. dissolutionthe solid residue was dissolved in methylene chloride
  5. customThe solution obtained
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-9a552e9af5304e8f8846a2c4bb8ce501
Source dataset
uspto-grants-2014_05
Patent number
US08716312B2

Reaction notes

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