2,3-Diaminophenol → HCID 178435562, compound

HRID 2182349Notes

Reaction equation

HRID 2182349 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:8]=O)[NH:6][N:7]=1)[CH3:2].[NH2:10][C:11]1[C:16]([NH2:17])=[CH:15][CH:14]=[CH:13][C:12]=1[OH:18].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C(O)C>[CH2:1]([C:3]1[CH:4]=[C:5]([C:8]2[NH:17][C:16]3[CH:15]=[CH:14][CH:13]=[C:12]([OH:18])[C:11]=3[N:10]=2)[NH:6][N:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 5799372,3-DiaminophenolHCID 656671Sodium PyrosulfiteHCID 178436696HCID 178436696, compound

Product 1

HCID 178435562HCID 178435562, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Starting with 100 mg of 5-ethyl-2H-pyrazole-3-carboxaldehyde, 100 mg of 2,3-diaminophenol, and 153 mg of sodium metabisulphite, in 1 ml of ethanol and 3 ml of dimethylformamide, and after purification by SPE (SCX phase, washing with methanol, extraction with 2N ammoniacal methanol) followed by a reverse-phase HPLC (5 mm, C18 phase, dimensions: 100×25 mm, flow rate 20 ml/min, elution gradient: acetonitrile/0.07% TFA-water/0.07% TFA from 5-95 to 95-5 (v/v)), and desalification by SPE (SCX phase, washing with methanol, extraction with 2N ammoniacal methanol), 16 mg of 2-(5-ethyl-2H-pyrazol-3-yl)-4-hydroxy-1H-benzimidazole are obtained in the form of a brown lacquer, the characteristics of which are as follows:

Workup

  1. custom3 ml of dimethylformamide, and after purification
  2. washby SPE (SCX phase, washing with methanol, extraction with 2N ammoniacal methanol)
  3. washC18 phase, dimensions: 100×25 mm, flow rate 20 ml/min, elution gradient
  4. washacetonitrile/0.07% TFA-water/0.07% TFA from 5-95 to 95-5 (v/v)), and desalification by SPE (SCX phase, washing with methanol, extraction with 2N ammoniacal methanol), 16 mg of 2-(5-ethyl-2H-pyrazol-3-yl)-4-hydroxy-1H-benzimidazole
  5. customare obtained in the form of a brown lacquer

Sources & evidence

ORD record
ord-db4fdddf99c84276924df2210f24336b
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

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