Sodium Pyrosulfite → HCID 178435557, compound

HRID 2064585Notes

Reaction equation

HRID 2064585 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:8]=O)[NH:6][N:7]=1)[CH3:2].[CH2:10]1[CH2:19][O:18][C:17]2[CH:16]=[CH:15][C:14]([NH2:20])=[C:13]([NH2:21])[C:12]=2[O:11]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:20][C:14]3[CH:15]=[CH:16][C:17]4[O:18][CH2:19][CH2:10][O:11][C:12]=4[C:13]=3[N:21]=2)[NH:6][N:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 656671Sodium PyrosulfiteHCID 43904631,2-Diamino-3,4-ethylenedioxybenzeneHCID 178436696HCID 178436696, compound

Product 1

HCID 178435557HCID 178435557, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Starting with 100 mg of 5-ethyl-2H-pyrazole-3-carboxaldehyde, 134 mg of 3,4-ethylenedioxy-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 m/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), 60 mg of 2-(5-ethyl-2H-pyrazol-3-yl)-4,5-ethylenedioxy-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 m/min, elution gradient acetonitrile/0.07% TFA-water/0.07% TFA from 5-95 to 95-5 (v/v)), and desalification
  4. washby SPE (SCX phase, washing with methanol, extraction with 2N ammoniacal methanol), 60 mg of 2-(5-ethyl-2H-pyrazol-3-yl)-4,5-ethylenedioxy-1H-benzimidazole
  5. customare obtained in the form of a brown lacquer

Sources & evidence

ORD record
ord-6ab0eb8d1e854b569f6fdd8745489de3
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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