Chloric acid → HCID 178467382, compound

HRID 1707657Notes

Reaction equation

HRID 1707657 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:29]2[NH:33][N:32]=[N:31][N:30]=2)[N:5]([C:7]2[CH:28]=[CH:27][C:10]([CH2:11][N:12]3[C:16]4=[N:17][CH:18]=[CH:19][C:20]([CH3:21])=[C:15]4[N:14]=[C:13]3S(CC)(=O)=O)=[CH:9][CH:8]=2)[CH:6]=1.[O-:34][CH2:35][CH3:36].[Na+].Cl(O)(=O)=O>C(O)C.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:29]2[NH:30][N:31]=[N:32][N:33]=2)[N:5]([C:7]2[CH:8]=[CH:9][C:10]([CH2:11][N:12]3[C:16]4=[N:17][CH:18]=[CH:19][C:20]([CH3:21])=[C:15]4[N:14]=[C:13]3[O:34][CH2:35][CH3:36])=[CH:27][CH:28]=2)[CH:6]=1

Participants

6

Reactant 3

HCID 19654Chloric acidHCID 2723922Sodium ethoxideHCID 178477665HCID 178477665, compound

Product 1

HCID 178467382HCID 178467382, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-[4-[4-chloro-2-(1H-tetrazol-5-yl)-1-pyrrolyl]benzyl]-2-ethylsulfonyl-7-methyl-3H-imidazo[4,5-b]pyridine (209 mg) in ethanol(2 ml) was added 1N sodium ethoxide solution in ethanol (1.02 ml) and dichloromethane(30 ml) at room temperature and the resulting mixture was heated under reflux for two hours. After cooling, the mixture was treated with 7% aqueous hydrogenchloric acid and the organic phase was washed with water and dried over anhydrous magnesium sulfute. After filtration the solvent was removed in vauo and the residue was purified by preparative thin layer chromatography eluting with dichloromethane-methanol(8:1 v/v) to give 3-[4-[4-chloro-2-(1H-tetrazol-5-yl)-1-pyrrolyl]benzyl]-2-ethoxy-7-methyl-3H-imidazo[4,5-b]pyridine(97 mg) as a amorphous solid which was powderized by treating with diethylether.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for two hours
  3. temperatureAfter cooling
  4. washthe organic phase was washed with water
  5. dry with materialdried over anhydrous magnesium sulfute
  6. filtrationAfter filtration the solvent
  7. customwas removed in vauo
  8. customthe residue was purified by preparative thin layer chromatography
  9. washeluting with dichloromethane-methanol(8:1 v/v)

Sources & evidence

ORD record
ord-a3051c1c63de49f9ba022389c12bb49d
Source dataset
uspto-grants-1994_10
Patent number
US05354759

Reaction notes

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