Water → HCID 9906201, compound

HRID 987478Notes

Reaction equation

HRID 987478 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([NH:6][C:7](=[O:17])[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:9]2)=[CH:4][C:3]=1[Cl:18].C[O:20][CH:21]1[CH:25]([CH:26]=O)[CH2:24][CH:23](OC)O1.O.C(OCC)(=O)C.CCCCCC>C(O)(=O)C>[Cl:18][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[N:1]1[CH:23]=[CH:24][C:25]([CH:21]=[O:20])=[CH:26]1)[N:9]=[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7](=[O:17])[NH:6]2

Participants

6

Reactant 4

HCID 962WaterHCID 567310Tetrahydro-2,5-dimethoxyfuran-3-carbaldehydeHCID 11346186HCID 11346186, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 9906201HCID 9906201, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of ethyl 7-amino-6-chloro-3,4-dihydro-3-oxoquinoxaline-2-carboxylate (500mg, 1.87 mmol) in acetic acid (10 ml) was added dropwise 2,5-dimethoxytetrahydrofuran-3-aldehyde (318 μl, 2.24 mmol) at 50° C., and the mixture was stirred for 40 minutes at the same temperature. The reaction mixture was poured into water (100 ml), which was extracted with ethyl acetate. After dried over anhydrous sodium sulfate, solvent was distilled off. The residue obtained was submitted to silica gel column chromatography [ethyl acetate-hexane=3:2] to obtain 166 mg of title compound as yellowish brown oily product. Yield 26%.

Workup

  1. extractionwas extracted with ethyl acetate
  2. dry with materialAfter dried over anhydrous sodium sulfate, solvent
  3. distillationwas distilled off
  4. customThe residue obtained

Sources & evidence

ORD record
ord-f1960198137b4251b001409912ab2749
Source dataset
uspto-grants-2003_10
Patent number
US06632813B1

Reaction notes

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