Isopropylamine → HCID 22341128, compound

HRID 584671Notes

Reaction equation

HRID 584671 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[C:7](O)[C:6](O)=[N:5]2.[N+:15]([O-:18])([O-])=[O:16].[Na+].C(=O)([O-])[O-].[Cs+].[Cs+].[CH:26]([NH2:29])([CH3:28])[CH3:27].[Na+].[CH3:31][S:32]([O-:34])=[O:33]>S(=O)(=O)(O)O.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N+:15]([O-:18])=[O:16])[C:11]=1[Cl:12])[N:8]=[C:7]([NH:29][CH:26]([CH3:28])[CH3:27])[C:6]([S:32]([CH3:31])(=[O:34])=[O:33])=[N:5]2

Participants

8

Reactant 5

HCID 6363IsopropylamineHCID 10796Cesium carbonateHCID 24268Sodium NitrateHCID 2733271Sodium methanesulfinateHCID 178517238HCID 178517238, compound

Product 1

HCID 22341128HCID 22341128, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of 6,7-dichloroquinoxaline-2,3-diol (1.0 g, 4.3 mmol) in concentrated sulfuric acid (20 ml) at 0° C. was added sodium nitrate (554 mg, 6.5 mmol) in portions over 15 minutes. The reaction mixture was stirred overnight at room temperature. The reaction was quenched by slowly pipetting into ice water. The precipitate was collected by vacuum filtration and the beige solid was washed with water. The nitrated product was suspended in phosphorous oxychloride, about 6 ml of DMF was added to make it homogeneous and the reaction was heated at reflux overnight. The reaction was quenched by slowly pipetting into ice water. The aqueous mixture was then extracted twice with ethyl acetate. The organic layers were combined and concentrated in vacuo to a beige solid. To a solution of the chlorinated product (1.57 g, crude) in DMF was added caesium carbonate (2.36 g, 7.2 mmol) followed by isopropyl amine (0.31 ml). The reaction mixture was stirred overnight at room temperature. The solvent was removed in vacuo. The solid was taken up in water and ethyl acetate. The layers were separated and the aqueous layer was extracted twice with ethyl acetate. The organic layers were combined and concentrated to a yellow solid that was purified by flash column chromatography using ethyl acetate:hexane 1:10. To a solution of the aminated product (588 mg, 1.7 mmol) in DMF (20 ml) was added methanesulfinic acid sodium salt (215 mg, 2.1 mmol). The solution was stirred overnight at room temperature. The final product was purified by flash column chromatography using ethyl acetate:hexane 1:5 obtaining the title compound as a yellow solid.

Workup

  1. customThe reaction was quenched
  2. filtrationThe precipitate was collected by vacuum filtration
  3. washthe beige solid was washed with water
  4. additionabout 6 ml of DMF was added
  5. temperaturethe reaction was heated
  6. temperatureat reflux overnight
  7. customThe reaction was quenched
  8. extractionThe aqueous mixture was then extracted twice with ethyl acetate
  9. concentrationconcentrated in vacuo to a beige solid
  10. stirringThe reaction mixture was stirred overnight at room temperature
  11. customThe solvent was removed in vacuo
  12. customThe layers were separated
  13. extractionthe aqueous layer was extracted twice with ethyl acetate
  14. concentrationconcentrated to a yellow solid
  15. customthat was purified by flash column chromatography
  16. stirringThe solution was stirred overnight at room temperature
  17. customThe final product was purified by flash column chromatography

Sources & evidence

ORD record
ord-541d856ac62a414ba77ffaa562505fff
Source dataset
uspto-grants-2005_08
Patent number
US06927214B1

Reaction notes

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