Water → HCID 18369188, compound

HRID 1699724Notes

Reaction equation

HRID 1699724 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([NH:6][C:7](=[O:17])[CH:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:9]2)=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19].C[O:23][CH:24]1[CH:28]([CH:29]=O)[CH2:27][CH:26](OC)O1.O>C(O)(=O)C>[CH:24]([C:28]1[CH:27]=[CH:26][N:1]([C:2]2[CH:11]=[C:10]3[C:5]([NH:6][C:7](=[O:17])[CH:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:9]3)=[CH:4][C:3]=2[C:18]([F:21])([F:20])[F:19])[CH:29]=1)=[O:23]

Participants

5

Reactant 3

HCID 962WaterHCID 567310Tetrahydro-2,5-dimethoxyfuran-3-carbaldehydeHCID 18369200HCID 18369200, compound

Product 1

HCID 18369188HCID 18369188, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of ethyl 7-amino-3-oxo-1,2,3,4-tetrahydro-6-trifluoromethylquinoxaline-2-carboxylate (3.60 g, 11.9 mmol) in acetic acid (60 ml) was added dropwise 2,5-dimethoxytetrahydrofuran-3-aldehyde (2.01 ml, 14.2 mmol) at 50° C., and the mixture was stirred for 1.5 hours at the same temperature. The reaction mixture was poured into water (300 ml), which was extracted with ethyl acetate. After dried over anhydrous sodium sulfate, solvent was distilled off. Methylene chloride was added to the residue obtained and the crystals were collected by filtration. These were washed with methylene chloride and then air-dried to obtain 2.57 g of the title compound as yellow powder. The filtrate and the washings were combined, concentrated under reduced pressure, and purified by means of silica gel column chromatography [ethyl acetate-hexane=2:1] to obtain further 973 mg. Total yield by weight 3.54 g. Yield 78%.

Workup

  1. extractionwas extracted with ethyl acetate
  2. dry with materialAfter dried over anhydrous sodium sulfate, solvent
  3. distillationwas distilled off
  4. additionMethylene chloride was added to the residue
  5. customobtained
  6. filtrationthe crystals were collected by filtration
  7. washThese were washed with methylene chloride
  8. customair-dried

Sources & evidence

ORD record
ord-14317a3db84c4665b79757032ebccffb
Source dataset
uspto-grants-2002_02
Patent number
US06348461B1

Reaction notes

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