Metronidazole → HCID 70170430, compound

HRID 2230072Notes

Reaction equation

HRID 2230072 reaction equation
[C:1]1([C:7]2[CH:16]=[C:15]([C:17]([OH:19])=[O:18])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:20][C:21]1[N:25](CCO)[C:24]([N+:29]([O-:31])=[O:30])=[CH:23][N:22]=1.[CH3:32][CH2:33]N=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.C1COCC1>[CH3:20][C:21]1[NH:25][C:24]([N+:29]([O-:31])=[O:30])=[CH:23][N:22]=1.[C:1]1([C:7]2[CH:16]=[C:15]([C:17]([O:19][CH2:32][CH3:33])=[O:18])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 4173MetronidazoleHCID 8593CinchophenHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

Product 1

HCID 70170430HCID 70170430, compoundYield 76.62%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The reaction mixture of 2-Phenyl-4-quinolinecarboxylic acid (274 mg, 1.1 mmol), metronidazole (171 mg, 1.0 mmol), EDCI (228 mg, 1.2 mmol), DMAP (20 mg, 0.2 mmol) and THF (5 ml) was stirred at room temperature for 10 h. THF was then removed under reduced pressure. The residue was dissolved in ethyl acetate. The organic layer was washed with H2O, 5% Na2CO3, H2O, and brine, and then dried over MgSO4. The solvent was removed under vacuum. The resulting solid was recrystallized from C2H5OH to give 305 mg (76.62%) 2-methyl-5-nitro-1H-imidazole-1-ethyl 2-phenyl-4-quinolinecarboxylate. m.p.: 122-124° C.

Workup

  1. customTHF was then removed under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washThe organic layer was washed with H2O, 5% Na2CO3, H2O, and brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed under vacuum
  6. customThe resulting solid was recrystallized from C2H5OH

Sources & evidence

ORD record
ord-b3281bfa1b3b41b3be56534282466386
Source dataset
uspto-grants-2002_07
Patent number
US06423707B1

Reaction notes

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