Sodium Iodide → HCID 15292078, compound

HRID 263723Notes

Reaction equation

HRID 263723 reaction equation
[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[Cl:9][C:10]1[N:15]=[C:14]([N:16]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:13]2[N:31]=[C:32]([CH3:34])[NH:33][C:12]=2[C:11]=1[CH3:35].[CH2:36]([O:38][CH2:39][CH2:40]Br)[CH3:37]>CC(C)=O>[Cl:9][C:10]1[N:15]=[C:14]([N:16]([CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:13]2[N:31]=[C:32]([CH3:34])[N:33]([CH2:37][CH2:36][O:38][CH2:39][CH3:40])[C:12]=2[C:11]=1[CH3:35]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 611412-Bromoethyl ethyl etherHCID 178432314HCID 178432314, compound

Product 1

HCID 15292078HCID 15292078, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Sodium iodide (1.5 g) and potassium carbonate (1 g) were added to a solution of 6-chloro-2,7-dimethyl-N4,N4 -bis(phenylmethyl)-1H-imidazo[4,5-c]pyridin-4-amine (1.0 g, 2.7 mmole) in acetone (250 mL). 2-Bromoethyl ethyl ether (0.5 mL, 4.4 mmole) was added and the reaction mixture was heated at reflux overnight. The reaction mixture was filtered and the filtrate concentrated under vacuum. The residue was partitioned between methylene chloride and water. The methylene chloride phase was separated, dried with magnesium sulfate and concentrated under vacuum. The residue was purified by silica gel column chromatography eluting with 10-30% ethyl acetate in hexane to provide 0.7 g of the desired product.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux overnight
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate concentrated under vacuum
  5. customThe residue was partitioned between methylene chloride and water
  6. customThe methylene chloride phase was separated
  7. dry with materialdried with magnesium sulfate
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by silica gel column chromatography
  10. washeluting with 10-30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-3fc826990d48416ab9bd99344d812ec3
Source dataset
uspto-grants-1997_07
Patent number
US05644063

Reaction notes

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