Hydrochloric Acid → HCID 178441543, compound

HRID 21854Notes

Reaction equation

HRID 21854 reaction equation
Cl.[CH2:2]([C:6]1[N:7]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[NH:31][N:30]=[N:29][N:28]=3)=[CH:17][CH:16]=2)[CH:8]=[C:9]([CH2:11][CH2:12][NH2:13])[N:10]=1)[CH2:3][CH2:4][CH3:5].O.[C:33]([OH:37])(=[O:36])[CH:34]=O.[OH-].[Na+].Cl.O1CCOC[CH2:42]1>>[CH2:2]([C:6]1[N:7]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]3[NH:31][N:30]=[N:29][N:28]=3)=[CH:17][CH:16]=2)[C:8]2[CH:34]([C:33]([O:37][CH3:42])=[O:36])[NH:13][CH2:12][CH2:11][C:9]=2[N:10]=1)[CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 15620607Glyoxylic acid, monohydrateHCID 1784416472-n-butyl-4-(2-aminoethyl)-1-[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methylimidazole hydrochloride

Product 1

HCID 178441543HCID 178441543, compound

Conditions

Temperature
50 °C

Procedure

A mixture of 2-n-butyl-4-(2-aminoethyl)-1-[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methylimidazole hydrochloride (8.09 g), glyoxylic acid hydrate (1.73 g), 1N aqueous sodium hydroxide solution (53 ml) and dioxane (50 ml) is stirred at 50° C. for two days. The reaction solution is acidified with hydrochloric acid, and evaporated under reduced pressure. The residue is dissolved in methanol (100 ml), and the mixture is cooled to -30° C., and thereto is added dropwise thionyl chloride (12.4 g). After addition, the mixture is stirred at 60° C. for two days. The mixture is evaporated under reduced pressure to remove the solvent. The mixture is neutralized with aqueous sodium hydrogen carbonate solution, and extracted with chloroform. The extract is dried, and evaporated under reduced pressure, and the resulting oily product is purified by silica gel column chromatography (solvent; chloroform/methanol=15:1) to give 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 (3.74 g) as a powder.

Workup

  1. customevaporated under reduced pressure
  2. dissolutionThe residue is dissolved in methanol (100 ml)
  3. temperaturethe mixture is cooled to -30° C.
  4. additionis added dropwise thionyl chloride (12.4 g)
  5. additionAfter addition
  6. stirringthe mixture is stirred at 60° C. for two days
  7. customThe mixture is evaporated under reduced pressure
  8. customto remove the solvent
  9. extractionextracted with chloroform
  10. customThe extract is dried
  11. customevaporated under reduced pressure
  12. customthe resulting oily product is purified by silica gel column chromatography (solvent; chloroform/methanol=15:1)

Sources & evidence

ORD record
ord-16151cf7586049c2b9696e6c4268ceff
Source dataset
uspto-grants-1995_06
Patent number
US05424316

Reaction notes

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