Chloroform → HCID 178468440, compound

HRID 1655125Notes

Reaction equation

HRID 1655125 reaction equation
[CH2:1]([C:3]1[N:16]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]3[N:34](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:33]=[N:32][N:31]=3)=[CH:20][CH:19]=2)[C:6]2C(C(OCC)=O)[NH:8][CH2:9][CH2:10][C:5]=2[N:4]=1)[CH3:2].[C:54]([O:57][C:58](=[O:60])[CH3:59])(=O)[CH3:55].[C:61](=[O:64])([O-])O.[Na+].[CH:66](Cl)(Cl)Cl>O>[CH2:1]([C:3]1[N:16]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]3[NH:34][N:33]=[N:32][N:31]=3)=[CH:20][CH:19]=2)[C:6]2[CH:59]([C:58]([O:57][CH2:54][CH3:55])=[O:60])[N:8]([C:61](=[O:64])[CH3:66])[CH2:9][CH2:10][C:5]=2[N:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 19932986ethyl 2-ethyl-3-[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylate

Product 1

HCID 178468440HCID 178468440, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 2-ethyl-3-[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylate (1.51 g), acetic anhydride (0.44 g), sodium hydrogen carbonate (1.09 g), chloroform (18 ml) and water (18 ml) is stirred overnight at room temperature. The aqueous layer is extracted with chloroform, and the combined organic layer is washed with aqueous citric acid solution and brine, dried, and evaporated. To the residue (1.46 g) is added fumaric acid (1.2 g) and ethanol (20 ml), and the mixture is refluxed for four hours, then evaporated. The residue is treated with a saturated sodium hydrogen carbonate solution and then extracted with chloroform. The organic layer is dried and evaporated. Purification by silica gel column chromatography (solvent; chloroform/methanol) gives ethyl 2-ethyl-5-acetyl-3-[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylate (0.76 g) as a white foam.

Workup

  1. extractionThe aqueous layer is extracted with chloroform
  2. washthe combined organic layer is washed with aqueous citric acid solution and brine
  3. customdried
  4. customevaporated
  5. additionTo the residue (1.46 g) is added fumaric acid (1.2 g) and ethanol (20 ml)
  6. temperaturethe mixture is refluxed for four hours
  7. customevaporated
  8. additionThe residue is treated with a saturated sodium hydrogen carbonate solution
  9. extractionextracted with chloroform
  10. customThe organic layer is dried
  11. customevaporated
  12. customPurification by silica gel column chromatography (solvent; chloroform/methanol)

Sources & evidence

ORD record
ord-2c6327a232fb47babcd900b9071bef9e
Source dataset
uspto-grants-1995_04
Patent number
US05409936

Reaction notes

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