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

HRID 1173866

Reaktionsgleichung

Reaktionsgleichung von HRID 1173866
[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.C([N:43]1[CH2:49][CH2:48][CH2:47][C@@H:44]1[CH:45]=O)(OC(C)(C)C)=O.[C:50]([BH3-])#[N:51].[Na+].[C:54](O)(=O)[CH3:55]>CO>[CH2:26]([N:51]([CH2:50][CH2:54][CH3:55])[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)[CH2:45][C@H:44]2[CH2:47][CH2:48][CH2:49][NH:43]2)=[CH:28][CH:27]=1)[CH2:27][CH3:28]

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 9005Trimethyl orthoformateHCID 5003444Sodium cyanoborohydrideHCID 7009153N-(tert-Butoxycarbonyl)-D-prolinalHCID 86599830HCID 86599830, Verbindung

Produkt 1

HCID 58801900N-(4-dipropylaminobutyl)-4-{[(1H-imidazol-2-ylmethyl)-(2R)-pyrrolidin-2-ylmethylamino]-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), N-Boc-D-prolinal (manufactured by Aldrich Corporation) (25.7 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 the residue was then 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). Then, the purified product was dissolved in methanol (500 μl) and added with a 4 mol/l hydrogen chloride/dioxane solution (500 μl), followed by stirring at room temperature for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure and the residue was then purified through silica gel column chromatography (chloroform/methanol), thereby obtaining hydrochloride (33.9 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 then 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. dissolutionThen, the purified product was dissolved in methanol (500 μl)
  10. additionadded with a 4 mol/l hydrogen chloride/dioxane solution (500 μl)
  11. stirringby stirring at room temperature for 2 hours
  12. customAfter completion of the reaction
  13. distillationthe solvent was distilled off under reduced pressure
  14. customthe residue was then purified through silica gel column chromatography (chloroform/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-b6c3b56029224f708691e6fb9bdc4df6
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07833991B2

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