4-Bromobenzene-1,2-diamine → HCID 178435558, compound

HRID 2064587Notes

Reaction equation

HRID 2064587 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:8]=O)[NH:6][N:7]=1)[CH3:2].[Br:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([NH2:18])[CH:12]=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:17][C:14]3[CH:15]=[CH:16][C:11]([Br:10])=[CH:12][C:13]=3[N:18]=2)[NH:6][N:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 3235934-Bromobenzene-1,2-diamineHCID 656671Sodium PyrosulfiteHCID 178436696HCID 178436696, compound

Product 1

HCID 178435558HCID 178435558, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Starting with 20 mg of 5-ethyl-2H-pyrazole-3-carboxaldehyde, 30 mg of 4-bromo-1,2-phenylenediamine and 30 mg of sodium metabisulphite, in 1 ml of ethanol and 2 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), 21 mg of 2-(5-ethyl-2H-pyrazol-3-yl)-5-bromo-1H-benzimidazole are obtained in the form of a yellow powder, the characteristics of which are as follows:

Workup

  1. custom2 ml of dimethylformamide, and after purification
  2. washby SPE (SCX phase, washing with methanol, extraction with 2N ammoniacal methanol)
  3. wash100×25 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), 21 mg of 2-(5-ethyl-2H-pyrazol-3-yl)-5-bromo-1H-benzimidazole
  5. customare obtained in the form of a yellow powder

Sources & evidence

ORD record
ord-78f07d3ffa0e4e33a3b3a1a9228e6c21
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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