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

HRID 348752
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 348752
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][NH:7][CH2:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:19][CH2:20][CH2:21][CH2:22][N:23]([CH2:27][CH2:28][CH3:29])[CH2:24][CH2:25][CH3:26])[CH:15]=2)[CH:10]=1.C([BH3-])#N.[Na+].C(O)(=O)C.[CH3:38][N:39]1[CH:43]=[CH:42][N:41]=[C:40]1[CH:44]=O>CO>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:19][CH2:20][CH2:21][CH2:22][N:23]([CH2:27][CH2:28][CH3:29])[CH2:24][CH2:25][CH3:26])[CH:15]=2)[CH:10]=1)[CH2:44][C:40]1[N:39]([CH3:38])[CH:43]=[CH:42][N:41]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 210843702-{[(1H-imidazol-2-ylmethyl)amino]methyl}-6-(4-dipropylaminobutyl)naphthalene

Produkt 1

HCID 588019122-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-6-(4-dipropylaminobutyl)-naphthalene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

The compound (39.0 mg) obtained in Example 124-5 was dissolved in anhydrous methanol (1.0 ml) and then added with sodium cyanoborohydride (9.40 mg), acetic acid (1.00 ml), and 1-methyl-2-imidazole carboxaldehyde (12.0 mg), followed by stirring at room temperature for 2 days under a nitrogen atmosphere. After completion of the reaction, the solvent was distilled off and the residue was then dissolved in chloroform. The solution was added with a saturated aqueous sodium bicarbonate solution and 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 and the solvent was then distilled off. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate) and treated with hydrochloric acid, thereby obtaining hydrochloride (16.7 mg) of the subject compound as a white solid.

Aufarbeitung

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. dissolutionthe residue was then dissolved in chloroform
  4. additionThe solution was added with a saturated aqueous sodium bicarbonate solution
  5. stirringstirred
  6. extractionThe solution was subjected to extraction with chloroform
  7. washthe extract was then washed with a saturated aqueous sodium bicarbonate solution and saturated saline solution
  8. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  9. distillationthe solvent was then distilled off
  10. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)
  11. additiontreated with hydrochloric acid

Quellen und Nachweise

ORD-Eintrag
ord-0156828164cf4d74a7c11c132cc8622a
Quelldatensatz
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07176227B2

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