Triethylamine → N-(7-bromo-2,3-dimethoxy-quinoxalin-5-ylmethyl)-oxalamic acid ethyl ester

HRID 1422227Notes

Reaction equation

HRID 1422227 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:13]=[C:12]([Br:14])[CH:11]=[C:10]2[C:5]=1[N:6]=[C:7]([O:17][CH3:18])[C:8]([O:15][CH3:16])=[N:9]2.C(N(CC)CC)C.[Cl-].[CH2:27]([O:29][C:30](=[O:34])[C:31](O)=[O:32])[CH3:28]>C1COCC1>[CH2:27]([O:29][C:30](=[O:34])[C:31]([NH:2][CH2:3][C:4]1[CH:13]=[C:12]([Br:14])[CH:11]=[C:10]2[C:5]=1[N:6]=[C:7]([O:17][CH3:18])[C:8]([O:15][CH3:16])=[N:9]2)=[O:32])[CH3:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18706309HCID 18706309, compoundHCID 23618337Oxalic acid monoethylester chloride

Product 1

HCID 54297612N-(7-bromo-2,3-dimethoxy-quinoxalin-5-ylmethyl)-oxalamic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

300 mg (1 mmol) of 5-aminomethyl-7-bromo-2,3-dimethoxyquinoxaline hydrochloride are suspended in 10 ml of THF and the suspension is cooled to 0° C. 0.183 ml (1.3 equiv.) of triethylamine is added and then 0.123 ml (1.1 equiv.) of oxalic acid monoethyl ester chloride is added dropwise in the course of 30 minutes. The mixture is stirred at 0° C. for 2 hours, then at 20° C. for 16 hours and is concentrated by evaporation. The residue is stirred in diethyl ether, and the solid is filtered off, washed with water and diethyl ether and dried.

Workup

  1. waitat 20° C. for 16 hours
  2. concentrationis concentrated by evaporation
  3. stirringThe residue is stirred in diethyl ether
  4. filtrationthe solid is filtered off
  5. washwashed with water and diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-3a4eeae901ef4f8f8829ea663f2041ce
Source dataset
uspto-grants-2000_06
Patent number
US06080743

Reaction notes

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