Trimethyl orthoformate → [4-(6-{[bis(1H-imidazol-2-ylmethyl)amino]methyl}-1-propyl-1H-benzimidazol-2-yl)butyl]dipropylamine

HRID 1174013Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1174013
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([CH2:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18])[N:8]([CH2:22][CH2:23][CH3:24])[C:7]=2[CH:25]=1.C(OC)(OC)OC.[NH:33]1[CH:37]=[CH:36][N:35]=[C:34]1[CH:38]=O.[BH4-].[Na+]>CO>[NH:33]1[CH:37]=[CH:36][N:35]=[C:34]1[CH2:38][N:1]([CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([CH2:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:16][CH2:17][CH3:18])[CH2:19][CH2:20][CH3:21])[N:8]([CH2:22][CH2:23][CH3:24])[C:7]=2[CH:25]=1)[CH2:11][C:9]1[NH:8][CH:7]=[CH:6][N:10]=1

Komponenten

6

Edukt 4

HCID 9005Trimethyl orthoformateHCID 249551H-imidazole-2-carbaldehydeHCID 4311764Sodium borohydrideHCID 23079304[4-(6-aminomethyl-1-propyl-1H-benzimidazol-2-yl)butyl]dipropylamine

Produkt 1

HCID 11577013[4-(6-{[bis(1H-imidazol-2-ylmethyl)amino]methyl}-1-propyl-1H-benzimidazol-2-yl)butyl]dipropylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The compound (130 mg) obtained in Example 125-6 was dissolved in methanol (3.0 ml) and added with trimethyl orthoformate (0.130 ml) and 2-imidazole carboxaldehyde (37.3 mg), followed by stirring for 1 hour. Then, the solution was cooled to 0° C. The solution was added with sodium borohydride (21.5 mg) and stirred at room temperature for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure and the residue was then dissolved in chloroform. The solution was washed with a 1 mol/l sodium hydroxide aqueous solution and then subjected to extraction with chloroform. The organic layer was washed with saturated saline solution and then dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure. Then, the residue was purified through silica gel column chromatography (chloroform/methanol) and treated with hydrochloric acid, thereby obtaining hydrochloride (16.4 mg) of the subject compound as a white solid.

Aufarbeitung

  1. stirringstirred at room temperature for 3 hours
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure
  4. dissolutionthe residue was then dissolved in chloroform
  5. washThe solution was washed with a 1 mol/l sodium hydroxide aqueous solution
  6. extractionsubjected to extraction with chloroform
  7. washThe organic layer was washed with saturated saline solution
  8. dry with materialdried with anhydrous sodium sulfate
  9. filtrationAfter filtration
  10. distillationthe solvent was distilled off under reduced pressure
  11. customThen, the residue was purified through silica gel column chromatography (chloroform/methanol)
  12. additiontreated with hydrochloric acid

Quellen und Nachweise

ORD-Eintrag
ord-2d91d952102644c29765b538d992bc31
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07833991B2

Notizen zur Reaktion

Wird geladen…