Metronidazole → HCID 131723409, compound

HRID 2230078Notes

Reaction equation

HRID 2230078 reaction equation
[N+:1]([C:4]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([N+]([O-])=O)[C:12]=3[N+:20]([O-:22])=[O:21])[C:7](=[N:26][O:27][CH:28]([CH3:32])[C:29]([OH:31])=[O:30])[C:6]=2[CH:5]=1)([O-:3])=[O:2].[CH3:33][C:34]1[N:38](CCO)[C:37]([N+:42]([O-:44])=[O:43])=[CH:36][N:35]=1.[CH3:45][CH2:46]N=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.C1COCC1>[CH3:33][C:34]1[NH:38][C:37]([N+:42]([O-:44])=[O:43])=[CH:36][N:35]=1.[N+:17]([C:15]1[CH:16]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]2[C:9]3[C:8](=[CH:13][C:12]([N+:20]([O-:22])=[O:21])=[CH:11][C:10]=3[N+:42]([O-:44])=[O:43])[C:7](=[N:26][O:27][CH:28]([CH3:32])[C:29]([O:31][CH2:45][CH3:46])=[O:30])[C:6]=2[CH:14]=1)([O-:19])=[O:18]

Participants

6

Reactant 3

HCID 4173MetronidazoleHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 87579249HCID 87579249, compound

Product 1

HCID 131723409HCID 131723409, compoundYield 106.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The reaction mixture of (+)-2-(2,4,5,6-tetranitro-9-fluorenylideneaminooxy)proprionic acid (223 mg, 0.5 mmol), metronidazole (86 mg, 0.5 mmol), EDCI (133 mg, 0.7 mmol), DMAP (10 mg, 0.1 mmol) and THF (5 ml) was stirred at room temperature for 6 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 liquid was separated by column chromatography to give 160 mg 2-methyl-5-nitro-1H-imidazole-1-ethyl (+)-2-(2,4,5,7-tetranitro-9-fluorenylideneaminooxy)propionate.

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 liquid was separated by column chromatography

Sources & evidence

ORD record
ord-90e6b60040d24129b1405a761f66ad67
Source dataset
uspto-grants-2002_07
Patent number
US06423707B1

Reaction notes

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