Water → 1-[(4-Methylphenyl)sulfonyl]-6-methyl-4H-imidazo[1,5,4-de]quinoxaline-2,5(1H,6H)-dione

HRID 551020Notes

Reaction equation

HRID 551020 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:21]3[C:22]4[N:13]([CH2:14][C:15](=[O:23])[NH:16][C:17]=4[CH:18]=[CH:19][CH:20]=3)[C:12]2=[O:24])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:25](=O)([O-])[O-].[K+].[K+].IC.O>CN(C=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:21]3[C:22]4[N:13]([CH2:14][C:15](=[O:23])[N:16]([CH3:25])[C:17]=4[CH:18]=[CH:19][CH:20]=3)[C:12]2=[O:24])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 576637421-[(4-Methylphenyl)sulfonyl]-4H-imidazo[1,5,4-de]quinoxaline-2,5(1H,6H)-dione

Product 1

HCID 671729911-[(4-Methylphenyl)sulfonyl]-6-methyl-4H-imidazo[1,5,4-de]quinoxaline-2,5(1H,6H)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1-[(4-methylphenyl)sulfonyl]-4H-imidazo[1,5,4-de]quinoxaline-2,5(1H,6H)-dione from Step D (1.16 g, 3.38 mmol) in DMF (40 mL) was added potassium carbonate (467 mg, 3.38 mmol) and the resulting mixture was stirred at ambient temperature for 10 min. Iodomethane (480 mg, 3.38 mmol) was added dropwise and the reaction mixture was stirred for 18 h, then poured into H2O (50 mL). The resulting precipitate was isolated by filtration, washed with H2O, and dried in vacuo to give the title compound. MS: m/z=358 (M+1).

Workup

  1. stirringthe reaction mixture was stirred for 18 h
  2. customThe resulting precipitate was isolated by filtration
  3. washwashed with H2O
  4. customdried in vacuo

Sources & evidence

ORD record
ord-dee22c76b6ae45498bf5c16ed1c87f4e
Source dataset
uspto-grants-2011_05
Patent number
US07947677B2

Reaction notes

Loading…