Metronidazole → HCID 70170973, compound

HRID 2230077Notes

Reaction equation

HRID 2230077 reaction equation
[CH3:1][CH2:2][N:3]1[C:9]2[N:10]=[C:11]([CH3:14])[CH:12]=[CH:13][C:8]=2[C:6](=[O:7])[C:5]([C:15]([OH:17])=[O:16])=[CH:4]1.[CH3:18][C:19]1[N:23](CCO)[C:22]([N+:27]([O-:29])=[O:28])=[CH:21][N:20]=1.[CH3:30][CH2:31]N=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.C1COCC1>[CH3:18][C:19]1[NH:23][C:22]([N+:27]([O-:29])=[O:28])=[CH:21][N:20]=1.[CH2:2]([N:3]1[C:9]2[C:8](=[CH:13][CH:12]=[C:11]([CH3:14])[N:10]=2)[C:6](=[O:7])[C:5]([C:15]([O:17][CH2:30][CH3:31])=[O:16])=[CH:4]1)[CH3:1]

Participants

6

Reactant 3

HCID 4173MetronidazoleHCID 4421Nalidixic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

Product 1

HCID 70170973HCID 70170973, compoundYield 14.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The reaction mixture of nalidixic acid (232 mg, 1.0 mmol), metronidazole (171 mg, 1.0 mmol), EDCI (230 mg, 1.2 mmol), DMAP (20 mg, 0.2 mmol) and THF (5 ml) was stirred at room temperature for 24 h. THF was then removed under reduced pressure. The residue was dissolved in dichloromethane (50 ml). 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 and ethyl acetate to give 56 mg 2-methyl-5-nitro-1H-imidazole-1-ethyl 1-ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate. m.p.: 122-124° C.

Workup

  1. customTHF was then removed under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane (50 ml)
  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 and ethyl acetate

Sources & evidence

ORD record
ord-e9392f5f31af43568c1513ead2104e52
Source dataset
uspto-grants-2002_07
Patent number
US06423707B1

Reaction notes

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