Acetic Acid → HCID 22387962, compound

HRID 1699957Notes

Reaction equation

HRID 1699957 reaction equation
[C:1]1([S:7]([NH:10][C:11]([C:13]2[N:18]=[C:17]3[N:19]([CH2:23][C:24]4[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[CH:26][C:25]=4[Cl:33])[C:20]([CH3:22])=[N:21][C:16]3=[CH:15][CH:14]=2)=[O:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)C>C(O)C>[NH2:30][C:27]1[CH:28]=[CH:29][C:24]([CH2:23][N:19]2[C:17]3=[N:18][C:13]([C:11](=[O:12])[NH:10][S:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)(=[O:8])=[O:9])=[CH:14][CH:15]=[C:16]3[N:21]=[C:20]2[CH3:22])=[C:25]([Cl:33])[CH:26]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 22388457HCID 22388457, compound

Product 1

HCID 22387962HCID 22387962, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-(Benzenesulfonylcarbamoyl)-3-(2-chloro-4-nitrobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine (245 mg) was suspended in ethanol (3 ml) and reduced iron (141 mg) and acetic acid (0.289 ml) were added, and the mixture was refluxed under heating overnight. The reaction mixture was filtered through Celite, and the filtrate was washed with a mixed solvent of methanol/chloroform (1/4) and the filtrate was concentrated under reduced pressure. To the concentrated residue were added a saturated aqueous sodium hydrogen carbonate solution, water and a mixed solvent of methanol/chloroform (1/4) and the aqueous phase was made alkaline. The precipitated insoluble matter was filtered through Celite and the filtrate was washed with a mixed solvent of methanol/chloroform (1/9). The filtrate was partitioned and the organic layer was dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure to give a crude product as a pale-brown powder. The crude product (100 mg) was recrystallized from N,N-dimethylformamide-water to give 3-(4-amino-2-chlorobenzyl)-5-(benzenesulfonylcarbamoyl)-2-methyl-3H-imidazo[4,5-b]pyridine (75 mg) as brown crystals.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating overnight
  3. filtrationThe reaction mixture was filtered through Celite
  4. washthe filtrate was washed with a mixed solvent of methanol/chloroform (1/4)
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionTo the concentrated residue were added a saturated aqueous sodium hydrogen carbonate solution, water
  7. filtrationThe precipitated insoluble matter was filtered through Celite
  8. washthe filtrate was washed with a mixed solvent of methanol/chloroform (1/9)
  9. customThe filtrate was partitioned
  10. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  11. filtrationfiltrated
  12. concentrationThe filtrate was concentrated under reduced pressure
  13. customto give a crude product as a pale-brown powder
  14. customThe crude product (100 mg) was recrystallized from N,N-dimethylformamide-water

Sources & evidence

ORD record
ord-fcb58a8d1a0e4c27881ce44564a5a9e8
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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