Diketene → HCID 178441547, compound

HRID 326458Notes

Reaction equation

HRID 326458 reaction equation
[CH2:1]([C:5]1[N:17]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[NH:35][N:34]=[N:33][N:32]=3)=[CH:21][CH:20]=2)[C:8]2[CH:9]([C:13]([O:15][CH3:16])=[O:14])[NH:10][CH2:11][CH2:12][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4].[CH2:36]=[C:37]1[O:41][C:39](=[O:40])[CH2:38]1>CO>[CH2:1]([C:5]1[N:17]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[NH:35][N:34]=[N:33][N:32]=3)=[CH:21][CH:20]=2)[C:8]2[CH:9]([C:13]([O:15][CH3:16])=[O:14])[N:10]([C:39](=[O:40])[CH2:38][C:37]([CH3:36])=[O:41])[CH2:11][CH2:12][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 12661DiketeneHCID 178441543HCID 178441543, compound

Product 1

HCID 178441547HCID 178441547, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of methyl 2-n-butyl-3-{2'-(1H-tetrazol-5-yl)biphenyl-4-yl}methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylate (0.50 g) and methanol (10 ml) is added diketene (0.20 g), and the mixture is stirred at room temperature for two hours. The solvent is distilled off under reduced pressure, and to the residue is added chloroform. The mixture is washed and dried, and evaporated under reduced pressure to remove the solvent. The resulting residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate/methanol) to give methyl 2-n-butyl-5-acetoacetyl-3-{2'-(1H-tetrazol-5-yl)biphenyl-4-yl}methyl-4,5,6,7-tetrahydroimidazo[4,5-c]-pyridine-4-carboxylate (0.29 g) as foam.

Workup

  1. distillationThe solvent is distilled off under reduced pressure
  2. additionto the residue is added chloroform
  3. washThe mixture is washed
  4. customdried
  5. customevaporated under reduced pressure
  6. customto remove the solvent
  7. customThe resulting residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate/methanol)

Sources & evidence

ORD record
ord-45c7b5616fa245ed82603ed3794c7d3f
Source dataset
uspto-grants-1993_12
Patent number
US05268377

Reaction notes

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