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Trimethyl orthoformate → 2-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-6-(3-dipropylaminopropyl)-naphtalene

HRID 1173994
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Reaktionsgleichung

Reaktionsgleichung von HRID 1173994
[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][N:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])[CH:9]=2)[CH:4]=1.C(OC)(OC)OC.[NH:30]1[CH:34]=[CH:33][N:32]=[C:31]1[CH:35]=O.[BH4-].[Na+].[Cl-].[NH4+].C([BH3-])#N.[Na+].[CH3:45][N:46]1[CH:50]=[CH:49][N:48]=[C:47]1[CH:51]=O>CO.C(O)(=O)C>[NH:30]1[CH:34]=[CH:33][N:32]=[C:31]1[CH2:35][N: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][N:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])[CH:9]=2)[CH:4]=1)[CH2:51][C:47]1[N:46]([CH3:45])[CH:50]=[CH:49][N:48]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 7

HCID 9005Trimethyl orthoformateHCID 249551H-imidazole-2-carbaldehydeHCID 25517Ammonium ChlorideHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 4311764Sodium borohydrideHCID 5003444Sodium cyanoborohydride
HCID 23079216
2-Aminomethyl-6-(3-dipropylaminopropyl)naphthalene

Produkt 1

HCID 100277962-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-6-(3-dipropylaminopropyl)-naphtalene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel2×

Versuchsvorschrift

The compound (280 mg) obtained in Example 121-11 was dissolved in anhydrous methanol (5.0 ml) and added with trimethyl orthoformate (0.154 ml) and 2-imidazole carboxaldehyde (90.1 mg), followed by stirring at room temperature for 2 hours under a nitrogen atmosphere. Subsequently, the solution was added with sodium borohydride (53.3 mg) in an ice bath and stirred at room temperature for 30 minutes. 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. The extract was washed with a saturated aqueous sodium bicarbonate solution and saturated saline solution. Then, the organic layer was dried with anhydrous sodium sulfate. The residue obtained was dissolved in anhydrous methanol (10 ml) and added with sodium cyanoborohydride (93.6 mg), acetic acid (3.00 ml), and 1-methyl-2-imidazole carboxaldehyde (120 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 then the solvent was distilled off. Subsequently, the residue was purified through silica gel column chromatography (chloroform/ethyl acetate) and treated with hydrochloric acid, thereby obtaining hydrochloride (318 mg) of the subject compound as a white solid.

Aufarbeitung

  1. stirringstirred at room temperature for 30 minutes
  2. customAfter completion of the reaction
  3. stirringthe whole was stirred
  4. extractionThe solution was subjected to extraction with chloroform
  5. washThe extract was washed with a saturated aqueous sodium bicarbonate solution and saturated saline solution
  6. dry with materialThen, the organic layer was dried with anhydrous sodium sulfate
  7. customThe residue obtained
  8. stirringby stirring at room temperature for 2 days under a nitrogen atmosphere
  9. customAfter completion of the reaction
  10. distillationthe solvent was distilled off
  11. dissolutionthe residue was then dissolved in chloroform
  12. additionThe solution was added with a saturated aqueous sodium bicarbonate solution
  13. stirringstirred
  14. extractionThe solution was subjected to extraction with chloroform
  15. washthe extract was then washed with a saturated aqueous sodium bicarbonate solution and saturated saline solution
  16. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  17. distillationthe solvent was distilled off
  18. customSubsequently, the residue was purified through silica gel column chromatography (chloroform/ethyl acetate)
  19. additiontreated with hydrochloric acid

Quellen und Nachweise

ORD-Eintrag
ord-f556abe4a06a4cb8b1f861fb70693015
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07833991B2

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