Dimethylformamide → 7-Acetyl-1-butyl-1,4,7,8,9,10-hexahydro-pyrido[3,2-f]quinoxaline-2,3-dione

HRID 48235Notes

Reaction equation

HRID 48235 reaction equation
[CH2:1]([N:5]1[C:14]2[C:13]3[CH2:15][CH2:16][CH2:17][NH:18][C:12]=3[CH:11]=[CH:10][C:9]=2[NH:8][C:7](=[O:19])[C:6]1=[O:20])[CH2:2][CH2:3][CH3:4].CN(C)C=O.ClCCl.[C:29](OC(=O)C)(=[O:31])[CH3:30]>C(N(CC)CC)C>[C:29]([N:18]1[C:12]2[CH:11]=[CH:10][C:9]3[NH:8][C:7](=[O:19])[C:6](=[O:20])[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:14]=3[C:13]=2[CH2:15][CH2:16][CH2:17]1)(=[O:31])[CH3:30]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 20633122HCID 20633122, compound

Product 1

HCID 227424857-Acetyl-1-butyl-1,4,7,8,9,10-hexahydro-pyrido[3,2-f]quinoxaline-2,3-dioneYield 19%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The product from Example 89 (0.14 g, 0.5 mmol) was solubilized in a minimal amount of dimethylformamide and then treated with 2 mL dichloromethane, acetic anhydride (0.15 g) and triethylamine (0.15 g). After the mixture stirred at room temperature for 18 h, it was poured onto dichloromethane/water. The aqueous layer was washed with dichloromethane and the combined organic layers over sodium sulfate, filtered and evaporated to give a dark syrup. The syrup was purified by silica gel chromatography (ethyl acetate as eluant) to give the title compound (30 mg, 19% yield).

Workup

  1. additionit was poured onto dichloromethane/water
  2. washThe aqueous layer was washed with dichloromethane
  3. filtrationthe combined organic layers over sodium sulfate, filtered
  4. customevaporated
  5. customto give a dark syrup
  6. customThe syrup was purified by silica gel chromatography (ethyl acetate as eluant)

Sources & evidence

ORD record
ord-2dc6125b3e9a45578597a614e14802c7
Source dataset
uspto-grants-2004_03
Patent number
US06703391B2

Reaction notes

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