Triethylamine → HCID 178472228, Verbindung

HRID 1655124

Reaktionsgleichung

Reaktionsgleichung von HRID 1655124
[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.CN(C)CCCN=C=NCC.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]

Komponenten

6

Edukt 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

Produkt 1

HCID 178472228HCID 178472228, VerbindungAusbeute 67,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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

Aufarbeitung

  1. washThe reaction mixture is washed with water
  2. dry with materialdried over sodium sulfate
  3. customevaporated
  4. dissolutionThe residue is dissolved in ethanol (30 ml)
  5. additionfumaric acid (2.00 g) is added
  6. temperaturethe solution is refluxed for three hours
  7. customThe solvent is evaporated
  8. additionthe residue is treated with a saturated sodium hydrogen carbonate solution
  9. extractionextracted with chloroform
  10. customThe organic layer is dried
  11. customevaporated
  12. customPurification by silica gel column chromatography (solvent; chloroform/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-d13e2af29efc4bc7915040a3b3e153b9
Quelldatensatz
uspto-grants-1995_04
Patentnummer
US05409936

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