Triethylamine → HCID 18706304, compound

HRID 1422211Notes

Reaction equation

HRID 1422211 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([O:14][CH3:15])[C:8]([O:12][CH3:13])=[N:9]2)=[C:4]([CH2:16]Br)[CH:3]=1.C(N(CC)CC)C.Cl.[C:26]([O:30][C:31](=[O:34])[CH2:32][NH2:33])([CH3:29])([CH3:28])[CH3:27]>C(#N)C>[C:26]([O:30][C:31](=[O:34])[CH2:32][NH:33][CH2:16][C:4]1[CH:3]=[C:2]([Br:1])[CH:11]=[C:10]2[C:5]=1[N:6]=[C:7]([O:14][CH3:15])[C:8]([O:12][CH3:13])=[N:9]2)([CH3:29])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 23298010HCID 23298010, compound

Product 1

HCID 18706304HCID 18706304, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

850 mg (2.35 mmol) of 7-bromo-5-bromomethyl-2,3-dimethoxy-quinoxaline, 0.982 ml of triethylamine and 719 mg of glycine tert-butyl ester hydrochloride are dissolved in 15 ml of acetonitrile and the solution is stirred at reflux for 18 hours. The mixture is concentrated by evaporation and the residue is dissolved in diethyl ether and washed with aqueous 5% sodium carbonate solution and brine. The organic phases are combined, dried over magnesium sulfate and concentrated by evaporation. The residue is chromatographed on silica gel with ethyl acetate and petroleum ether (1:2). The title compound is obtained in the form of a yellow oil.

Workup

  1. temperatureat reflux for 18 hours
  2. concentrationThe mixture is concentrated by evaporation
  3. dissolutionthe residue is dissolved in diethyl ether
  4. washwashed with aqueous 5% sodium carbonate solution and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated by evaporation
  7. customThe residue is chromatographed on silica gel with ethyl acetate and petroleum ether (1:2)

Sources & evidence

ORD record
ord-c594df89354644afb155b893db9dca5c
Source dataset
uspto-grants-2000_06
Patent number
US06080743

Reaction notes

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