Potassium Carbonate → HCID 178488910, compound

HRID 1647013Notes

Reaction equation

HRID 1647013 reaction equation
C(OC(=O)C[N:6]([C:17]1[CH:22]=[CH:21][C:20](OC)=[CH:19][CH:18]=1)[C:7]1[CH:16]=[N:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1)C.[C:26](=[O:29])([O-])[O-].[K+].[K+].[CH:32](N(C(C)C)CC)(C)C.[C:41](N1C=CN=C1)(N1C=CN=C1)=[O:42]>O.CO>[CH3:41][O:42][C:19]1[CH:20]=[CH:21][C:22]([C:17]2[C:26](=[O:29])[N:8]3[C:9]4[C:14]([NH:15][CH:16]=[C:7]3[N:6]=2)=[CH:13][CH:12]=[CH:11][CH:10]=4)=[CH:32][CH:18]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 19003561HCID 19003561, compound

Product 1

HCID 178488910HCID 178488910, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of DL-N-(2-quinoxalinyl)-4-methoxyphenylglycine ethyl ester (160 mg, 0.48 mmol), potassium carbonate (328 mg 2.37 mmol), methanol (1 mL) and water (3 mL) was stirred at reflux for 16 h. After neutralization with aqueous acetic acid the product was extracted with 10% methanol/ethyl acetate, the organic layer was dried over magnesium sulfate and the solvent was removed in vacuo. The residue was dissolved in methylene chloride (5 mL) and treated with diisopropylethylamine (0.16 mL, 1.0 mmol) and carbonyldiimidazole (405 mg, 2.5 mmol). After 3 h at room temperature the product was filtered and washed with ether to afford 2-(4-methoxyphenyl)-imidazo-[1,2-a]-quinoxalin-1(5H)-one (Compound 1) as orange crystals melting at 305°-306° C.

Workup

  1. temperatureat reflux for 16 h
  2. extractionAfter neutralization with aqueous acetic acid the product was extracted with 10% methanol/ethyl acetate
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. customthe solvent was removed in vacuo
  5. dissolutionThe residue was dissolved in methylene chloride (5 mL)
  6. filtrationAfter 3 h at room temperature the product was filtered
  7. washwashed with ether

Sources & evidence

ORD record
ord-93528ce949704b6a892926a6796a5db3
Source dataset
uspto-grants-1993_01
Patent number
US05182386

Reaction notes

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