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

HRID 48236Notes

Reaction equation

HRID 48236 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.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>C(N(CC)CC)C>[CH2:1]([N:5]1[C:14]2[C:13]3[CH2:15][CH2:16][CH2:17][N:18]([S:30]([CH3:29])(=[O:32])=[O:31])[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]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 20633122HCID 20633122, compound

Product 1

HCID 227424781-Butyl-1,4,7,8,9,10-hexahydro-7-methanesulfonyl-pyrido[3,2-f]quinoxaline-2,3-dioneYield 19%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The product from Example 89 (0.12 g, 0.45 mmol) was solubilized in a minimal amount of dimethylformamide and then treated with 2 mL dichloromethane, methanesulfonyl chloride (0.17 g) and triethylamine (0.15 g). After stirring at room temperature for 4 h, the mixture was washed with water, dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography (4:1 heptane:ethyl acetate as eluant) to give the title compound (30 mg, 17% yield).

Workup

  1. washthe mixture was washed with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by silica gel chromatography (4:1 heptane:ethyl acetate as eluant)

Sources & evidence

ORD record
ord-d8e18bfc599947a08809ca063f57ba63
Source dataset
uspto-grants-2004_03
Patent number
US06703391B2

Reaction notes

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