Triethylamine → HCID 178472228, compound

HRID 326462

Reaction equation

HRID 326462 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]2[CH:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:8][CH2:9][CH2:10][C:5]=2[N:4]=1)[CH3:2].[C:54]([O:60][CH2:61][CH3:62])(=[O:59])[CH2:55][C:56]([O-])=[O:57].Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>ClCCl>[CH2:1]([C:3]1[N:16]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]3[NH:31][N:32]=[N:33][N:34]=3)=[CH:22][CH:23]=2)[C:6]2[CH:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:8]([C:56](=[O:57])[CH2:55][C:54]([O:60][CH2:61][CH3:62])=[O:59])[CH2:9][CH2:10][C:5]=2[N:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 3595298Propanedioic acid, monoethyl esterHCID 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 178472228HCID 178472228, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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 (1.94 g), monoethyl malonate (0.74 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.80 g), and triethylamine (1.40 g) are dissolved in dichloromethane (20 ml). The mixture is stirred overnight at room temperature. The reaction mixture is washed with water, dried over sodium sulfate, and then evaporated to remove the solvent. The residue is dissolved in ethanol (30 ml) and thereto is added fumaric acid (2.00 g). The mixture is refluxed for three hours and evaporated to remove the solvent. The resulting residue is treated with a saturated sodium hydrogen carbonate solution and extracted with chloroform. The organic layer is dried and evaporated to remove the solvent. The resulting residue is purified by silica gel column chromatography (solvent; chloroform/methanol) to give ethyl 2-ethyl-3-{2'-(1H-tetrazol-5-yl)biphenyl-4-yl}methyl-5-ethoxycarbonylacetyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylate (1.07 g) as foam.

Workup

  1. washThe reaction mixture is washed with water
  2. dry with materialdried over sodium sulfate
  3. customevaporated
  4. customto remove the solvent
  5. dissolutionThe residue is dissolved in ethanol (30 ml)
  6. additionis added fumaric acid (2.00 g)
  7. temperatureThe mixture is refluxed for three hours
  8. customevaporated
  9. customto remove the solvent
  10. additionThe resulting residue is treated with a saturated sodium hydrogen carbonate solution
  11. extractionextracted with chloroform
  12. customThe organic layer is dried
  13. customevaporated
  14. customto remove the solvent
  15. customThe resulting residue is purified by silica gel column chromatography (solvent; chloroform/methanol)

Sources & evidence

ORD record
ord-833701a8ae6b41c19c84b0c7fe46144a
Source dataset
uspto-grants-1993_12
Patent number
US05268377

Linked notes

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