4-Methoxy-o-phenylenediamine → HCID 178435561, compound

HRID 2064586Notes

Reaction equation

HRID 2064586 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:8]=O)[NH:6][N:7]=1)[CH3:2].[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([NH2:19])[CH:13]=1.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:18][C:15]3[CH:16]=[CH:17][C:12]([O:11][CH3:10])=[CH:13][C:14]=3[N:19]=2)[NH:6][N:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 1534044-Methoxy-o-phenylenediamineHCID 656671Sodium PyrosulfiteHCID 178436696HCID 178436696, compound

Product 1

HCID 178435561HCID 178435561, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Starting with 100 mg of 5-ethyl-2H-pyrazole-3-carboxaldehyde, 138 mg of 4-methoxy-1,2-phenylenediamine, 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), 61 mg of 2-(5-ethyl-2H-pyrazol-3-yl)-5-methoxy-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), 61 mg of 2-(5-ethyl-2H-pyrazol-3-yl)-5-methoxy-1H-benzimidazole
  5. customare obtained in the form of a brown lacquer

Sources & evidence

ORD record
ord-d5f0aa7e6e464a01b7ae62091f02567f
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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