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Trimethyl orthoformate → 2-{[(1H-imidazol-2-ylmethyl)amino]methyl}-6-(4-dipropylaminobutyl)naphthalene

HRID 1174006
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1174006
[NH2:1][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:13][CH2:14][CH2:15][CH2:16][N:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])[CH:9]=2)[CH:4]=1.C(OC)(OC)OC.[NH:31]1[CH:35]=[CH:34][N:33]=[C:32]1[CH:36]=O.[BH4-].[Na+].[Cl-].[NH4+]>CO>[NH:31]1[CH:35]=[CH:34][N:33]=[C:32]1[CH2:36][NH:1][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:13][CH2:14][CH2:15][CH2:16][N:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])[CH:9]=2)[CH:4]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 9005Trimethyl orthoformateHCID 249551H-imidazole-2-carbaldehydeHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 210843902-Aminomethyl-6-(4-dipropylaminobutyl)naphthalene

Produkt 1

HCID 210843702-{[(1H-imidazol-2-ylmethyl)amino]methyl}-6-(4-dipropylaminobutyl)naphthalene
Ausbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

The compound (67.5 mg) obtained in Example 124-4 was dissolved in anhydrous methanol (2.0 ml) and added with trimethyl orthoformate (0.0354 ml) and 2-imidazole carboxaldehyde (20.8 mg), followed by stirring at room temperature for 2 hours under a nitrogen atmosphere. Subsequently, the solution was added with sodium borohydride (12.3 mg) in an ice bath and then stirred at room temperature for 1 hour. After completion of the reaction, a saturated aqueous ammonium chloride solution was added to the solution, and the whole was stirred. The solution was subjected to extraction with chloroform and the extract was then washed with a saturated aqueous sodium bicarbonate solution and saturated saline solution. The organic layer was dried with anhydrous sodium sulfate. The solvent was distilled off and the residue was then purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (39.0 mg) as a yellow oily substance.

Aufarbeitung

  1. stirringstirred at room temperature for 1 hour
  2. customAfter completion of the reaction
  3. stirringthe whole was stirred
  4. extractionThe solution was subjected to extraction with chloroform
  5. washthe extract was then washed with a saturated aqueous sodium bicarbonate solution and saturated saline solution
  6. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  7. distillationThe solvent was distilled off
  8. customthe residue was then purified through silica gel column chromatography (chloroform/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-e8fa738f29da466f9b72de1356f4ac18
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07833991B2

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