Acetic Acid → HCID 22614854, compound

HRID 842679Notes

Reaction equation

HRID 842679 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:5]([N:19]2[C:23]([C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)=[N:22][N:21]=[C:20]2C(OCC)=O)=[C:6]2[C:11](=[CH:12][C:13]=1[Cl:14])[N:10]=[C:9]([O:15][CH3:16])[C:8]([O:17][CH3:18])=[N:7]2.C(O)(=O)C>O1CCOCC1.O>[Cl:3][C:4]1[C:5]([N:19]2[CH:20]=[N:21][N:22]=[C:23]2[C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)=[C:6]2[C:11](=[CH:12][C:13]=1[Cl:14])[N:10]=[C:9]([O:15][CH3:16])[C:8]([O:17][CH3:18])=[N:7]2

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 22614908HCID 22614908, compound

Product 1

HCID 22614854HCID 22614854, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

1M Aqueous sodium hydroxide solution (17.25 mL, 17.25 mmol) was added dropwise to a stirred solution of 6,7-dichloro-2,3-dimethoxy-5-[3-ethoxycarbonyl-5-(3-pyridyl)-4H-1,2,4-triazol-4-yl]quinoxaline (Preparation 94, 8.2 g, 17.25 mmol) in 1,4-dioxane (68 mL) and water (50 mL) at 10° C. The solution was warmed to room temperature and stirred for 20 hours, diluted with water (50 mL), acidified with glacial acetic acid and extracted with ethyl acetate (1×100 mL, 2×50 mL). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, by gradient elution using dichloromethane:methanol (1:0 changing to 9:1, by volume) to give the title compound (5.82 g, 84%) as a white solid, mp 206-207° C.

Workup

  1. extractionextracted with ethyl acetate (1×100 mL, 2×50 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography on silica gel, by gradient elution

Sources & evidence

ORD record
ord-7ab1aac43d0c47e5b7a60d7f6980cd34
Source dataset
uspto-grants-2002_04
Patent number
US06376490B1

Reaction notes

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