HCID 19932982, compound → HCID 178439974, compound

HRID 326468Notes

Reaction equation

HRID 326468 reaction equation
[CH2:1]([C:4]1[N:5]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]3[N:29](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:28]=[N:27][N:26]=3)=[CH:15][CH:14]=2)[CH:6]=[C:7]([CH2:9][CH2:10][NH2:11])[N:8]=1)[CH2:2][CH3:3].O.[C:50]([O:54][CH2:55][CH3:56])(=[O:53])[CH:51]=[O:52].Cl.C([OH:60])C>O1CCCC1>[C:50]([OH:54])(=[O:53])[C:51]([OH:60])=[O:52].[CH2:1]([C:4]1[N:5]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]3[NH:29][N:28]=[N:27][N:26]=3)=[CH:15][CH:14]=2)[C:6]2[CH:51]([C:50]([O:54][CH2:55][CH3:56])=[O:53])[NH:11][CH2:10][CH2:9][C:7]=2[N:8]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 19932982HCID 19932982, compoundHCID 21887872Ethanol hydrochlorideHCID 22414697Ethyl glyoxylate hydrate

Product 1

HCID 178439974HCID 178439974, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 2-n-propyl-4-(2-aminoethyl)-1-{2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl}methylimidazole (21.95 g) and tetrahydrofuran (200 ml) is added a solution of ethyl glyoxylate hydrate (4.25 g) in tetrahydrofuran (20 ml) at 5° C. The mixture is stirred overnight at room temperature and refluxed for 30 minutes. To a mixture is added a 8% hydrogen chloride-ethanol solution (100 ml) at room temperature. The reaction mixture is stirred for 30 minutes, and evaporated to remove the solvent. The residue is dissolved in chloroform and washed successively with saturated sodium hydrogen carbonate solution and brine. The organic layer is dried and evaporated to remove the solvent. The crude residue is treated with a mixture of oxalic acid and ethanol to give ethyl 2-n-propyl-3-{2'-(1H-tetrazol-5-yl)biphenyl-4-yl}methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylate oxalate (10.84 g).

Workup

  1. temperaturerefluxed for 30 minutes
  2. stirringThe reaction mixture is stirred for 30 minutes
  3. customevaporated
  4. customto remove the solvent
  5. dissolutionThe residue is dissolved in chloroform
  6. washwashed successively with saturated sodium hydrogen carbonate solution and brine
  7. customThe organic layer is dried
  8. customevaporated
  9. customto remove the solvent
  10. additionThe crude residue is treated with a mixture of oxalic acid and ethanol

Sources & evidence

ORD record
ord-dec5cbcf6f9f482d9d647ae2e5a8473b
Source dataset
uspto-grants-1993_12
Patent number
US05268377

Reaction notes

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