Triethylamine → 2-Isobutylimidazo[1,2-a]quinoxalin-4-amine

HRID 1920953Notes

Reaction equation

HRID 1920953 reaction equation
Cl[C:2]1[C:11](Cl)=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C([N:15](CC)CC)C.[NH2:20][CH:21]([CH2:24][CH:25]([CH3:27])[CH3:26])[CH2:22]O>O1CCOCC1.C(OCC)(=O)C>[CH2:24]([C:21]1[N:20]=[C:2]2[C:11]([NH2:15])=[N:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]2[CH:22]=1)[CH:25]([CH3:27])[CH3:26]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 166592,3-DichloroquinoxalineHCID 790302-Amino-4-methylpentan-1-ol

Product 1

HCID 167420622-Isobutylimidazo[1,2-a]quinoxalin-4-amineYield 95.7%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 2,3-dichloroquinoxaline (2.0 g, 10.0 mmol) in 10 mL of 1,4-dioxane was added triethyl amine (1.81 g, 18 mmol) and followed by 2-amino-4-methylpentan-1-ol (1.4 g, 12 mmol). The reaction mixture was separated into 2 microwave tubes. And then the mixture was stirred in microwave for 10 minutes at 130° C. The combined reaction mixture was diluted with 150 mL of ethyl acetate and then was washed with water (20 mL), brine (20 mL), dried over MgSO4, filtered and concentrated. The crude product was purified by flash column chromatography eluted with ethyl acetate and hexanes to give the titled compound (2.3 g, 69%)

Workup

  1. customThe reaction mixture was separated into 2 microwave tubes
  2. customThe combined reaction mixture
  3. washwas washed with water (20 mL), brine (20 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash column chromatography
  8. washeluted with ethyl acetate and hexanes

Sources & evidence

ORD record
ord-8b826dda3e9c45dea92745717b62ccf6
Source dataset
uspto-grants-2012_05
Patent number
US08173657B2

Reaction notes

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