Ethanol → HCID 14499850, compound

HRID 2073809Notes

Reaction equation

HRID 2073809 reaction equation
[Cl-].[NH4+].[CH3:3][C:4]1[CH:27]=[CH:26][CH:25]=[C:24]([NH:28][C:29]([O:31][CH3:32])=[O:30])[C:5]=1[CH2:6][NH:7][C:8]1[C:9]2[N:10]([C:17]([CH2:21][C:22]#[CH:23])=[C:18]([CH3:20])[N:19]=2)[CH:11]=[C:12]([N+:14]([O-])=O)[CH:13]=1.[CH2:33]([OH:35])[CH3:34]>O.[Fe]>[CH3:3][C:4]1[CH:27]=[CH:26][CH:25]=[C:24]([NH:28][C:29]([O:31][CH3:32])=[O:30])[C:5]=1[CH2:6][NH:7][C:8]1[C:9]2[N:10]([C:17]([CH2:21][C:22]#[CH:23])=[C:18]([CH3:20])[N:19]=2)[CH:11]=[C:12]([NH:14][C:33](=[O:35])[CH3:34])[CH:13]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 14499838HCID 14499838, compound

Product 1

HCID 14499850HCID 14499850, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

To a mixture of iron powder (145 mg) and ammonium chloride (15 mg) in ethanol (12 ml) and water (2.2 ml) was added 8-(2-methyl-6-methoxycarbonylaminobenzylamino)-6-nitro-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine (360 mg) and the mixture was refluxed for 40 minutes. The inorgnic materials were removed by filtration and the solvent was evaporated under reduced pressure. An aqueous solution of sodium bicarbonate (5 ml) was added to the residue and the resultant solid was collected by filtration. The solid was dissolved in methylene chloride (10 ml) and acetic anhydride (94 mg) was added thereto. After stirring for 1 hour at room temperature, the organic layer was washed with an aqueous solution of sodium bicarbonate and then with water. The solvent was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel (10 g), eluting with a mixture of chloroform and methanol (100:3). The fractions containing the desired product were combined, and the solvent was removed under reduced pressure. The residue was triturated with a mixture of ethanol and diethyl ether (1:1) to give 8-(2-methyl-6-methoxycarbonylaminobenzylamino)-6-acetamido-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine (70 mg).

Workup

  1. temperaturethe mixture was refluxed for 40 minutes
  2. customThe inorgnic materials were removed by filtration
  3. customthe solvent was evaporated under reduced pressure
  4. additionAn aqueous solution of sodium bicarbonate (5 ml) was added to the residue
  5. filtrationthe resultant solid was collected by filtration
  6. dissolutionThe solid was dissolved in methylene chloride (10 ml)
  7. additionacetic anhydride (94 mg) was added
  8. washthe organic layer was washed with an aqueous solution of sodium bicarbonate
  9. customThe solvent was evaporated under reduced pressure
  10. washeluting with a mixture of chloroform and methanol (100:3)
  11. additionThe fractions containing the desired product
  12. customthe solvent was removed under reduced pressure
  13. customThe residue was triturated with a mixture of ethanol and diethyl ether (1:1)

Sources & evidence

ORD record
ord-7646f5964be642e3bbac648a591c7797
Source dataset
uspto-grants-1990_04
Patent number
US04920129

Reaction notes

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