Fumaric Acid → HCID 178439975, compound

HRID 1655132Notes

Reaction equation

HRID 1655132 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][C:6]2[N:9]=[C:10]([CH2:49][CH2:50][CH3:51])[N:11]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[C:25]4[N:29](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[N:28]=[N:27][N:26]=4)=[CH:15][CH:14]=3)[C:5]=2[CH:4]1[C:52]([O:54][CH2:55][CH3:56])=[O:53])[CH3:2].C(O)(=O)/C=C/C(O)=O>C(O)C>[CH2:1]([N:3]1[CH2:8][CH2:7][C:6]2[N:9]=[C:10]([CH2:49][CH2:50][CH3:51])[N:11]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[C:25]4[NH:29][N:28]=[N:27][N:26]=4)=[CH:15][CH:14]=3)[C:5]=2[CH:4]1[C:52]([O:54][CH2:55][CH3:56])=[O:53])[CH3:2]

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 15291715ethyl 5-ethyl-2-n-propyl-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 178439975HCID 178439975, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 5-ethyl-2-n-propyl-3-[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylate (1.10 g), fumaric acid (1.2 g) and ethanol (20 ml) is refluxed for one hour. The mixture is evaporated, and the residue is dissolved in chloroform, and the mixture is washed with a saturated sodium hydrogen carbonate solution and brine, dried and evaporated. The residue is purified by silica gel column chromatography (solvent; chloroform/methanol) to give ethyl 5-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 (0.65 g) as a white foam.

Workup

  1. temperatureis refluxed for one hour
  2. customThe mixture is evaporated
  3. dissolutionthe residue is dissolved in chloroform
  4. washthe mixture is washed with a saturated sodium hydrogen carbonate solution and brine
  5. customdried
  6. customevaporated
  7. customThe residue is purified by silica gel column chromatography (solvent; chloroform/methanol)

Sources & evidence

ORD record
ord-635fdf52b2614984926375052ba73ea2
Source dataset
uspto-grants-1995_04
Patent number
US05409936

Reaction notes

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