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

HRID 1920954Notes

Reaction equation

HRID 1920954 reaction equation
Cl[C:2]1[C:3]([NH:12][CH:13]([CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:14]O)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.C([N:22](CC)CC)C.O>CS(C)=O>[CH2:16]([C:13]1[N:12]=[C:3]2[C:2]([NH2:22])=[N:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]2[CH:14]=1)[CH:17]([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 574259072-(3-Chloroquinoxalin-2-ylamino)-4-methylpentan-1-ol

Product 1

HCID 167420622-Isobutylimidazo[1,2-a]quinoxalin-4-amineYield 76.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of the 2-(3-chloroquinoxalin-2-ylamino)-4-methylpentan-1-ol (1.90 g, 6.79 mmol) in 10 mL of DMSO was added triethyl amine (1.92 g, 19.0 mmol) and followed by sulfur trioxide pyridine complex (2.38 g, 14.9 mmol) at room temperature. The reaction mixture was stirred at that temperature overnight. And then 100 mL of water was added to reaction mixture. The resulting mixture was extracted with ethyl acetate (75 mL×2). The combined organic layers were 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 (1.25 g, 64%). MS: MH+=278:280=3:1

Workup

  1. customfollowed by sulfur trioxide pyridine complex (2.38 g, 14.9 mmol) at room temperature
  2. extractionThe resulting mixture was extracted with ethyl acetate (75 mL×2)
  3. washThe combined organic layers were 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-f38a188ddcef4bcf9db7d423bb685228
Source dataset
uspto-grants-2012_05
Patent number
US08173657B2

Reaction notes

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