Acetic Acid → N-(4-dipropylaminobutyl)-4-{[(1H-imidazol-2-ylmethyl)-(4-methyl-1H-imidazol-5-ylmethyl)-amino]-methyl}-benzamide

HRID 348616

Reaktionsgleichung

Reaktionsgleichung von HRID 348616
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][NH:7][CH2:8][C:9]1[CH:28]=[CH:27][CH:26]=[CH:25][C:10]=1C(NCCCCN(CCC)CCC)=O.C([O:34][CH3:35])(OC)OC.[CH3:36][C:37]1[N:38]=[CH:39][NH:40][C:41]=1[CH:42]=O.[C:44]([BH3-])#[N:45].[Na+].[C:48](O)(=O)[CH3:49]>CO>[CH2:26]([N:45]([CH2:44][CH2:48][CH3:49])[CH2:25][CH2:10][CH2:9][CH2:8][NH:7][C:35](=[O:34])[C:26]1[CH:25]=[CH:10][C:9]([CH2:8][N:7]([CH2:6][C:2]2[NH:1][CH:5]=[CH:4][N:3]=2)[CH2:36][C:37]2[NH:38][CH:39]=[N:40][C:41]=2[CH3:42])=[CH:28][CH:27]=1)[CH2:27][CH3:28]

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 9005Trimethyl orthoformateHCID 27958875-Methyl-1H-imidazole-4-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 86599830HCID 86599830, Verbindung

Produkt 1

HCID 178457213N-(4-dipropylaminobutyl)-4-{[(1H-imidazol-2-ylmethyl)-(4-methyl-1H-imidazol-5-ylmethyl)-amino]-methyl}-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

The compound (53.8 mg) obtained in Example 1-4 was dissolved in methanol (0.8 ml). Then, the solution was added with trimethyl orthoformate (50 μl), acetic acid (50 μl), and 4-methyl-5-imidazole carboxaldehyde (manufactured by Aldrich Corporation) (28.5 mg) and stirred at room temperature for 10 minutes. Subsequently, sodium cyanoborohydride (24.4 mg) was added, followed by stirring overnight at room temperature. The solvent was distilled off under reduced pressure and then the residue was dissolved in chloroform, followed by washing with 1 mol/l sodium hydroxide and saturated saline solution and drying with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure and the residue was then purified through silica gel column chromatography (chloroform/methanol) and then treated with hydrochloric acid, thereby obtaining hydrochloride (33.5 mg) of the subject compound as a white solid.

Aufarbeitung

  1. stirringby stirring overnight at room temperature
  2. distillationThe solvent was distilled off under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform
  4. washby washing with 1 mol/l sodium hydroxide and saturated saline solution
  5. dry with materialdrying with anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. distillationthe solvent was distilled off under reduced pressure
  8. customthe residue was then purified through silica gel column chromatography (chloroform/methanol)
  9. additiontreated with hydrochloric acid

Quellen und Nachweise

ORD-Eintrag
ord-72da7cd121a54b06b2959db25439e293
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176227B2

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