Sodium Hydroxide → N-[4-[(dipropylamino)methyl]phenyl]-4-[[1H-imidazol-2-ylmethyl(3-isoquinolylmethyl)amino]methyl]benzamide

HRID 1173896Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1173896
C(N(CCC)[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:27])[C:13]2[CH:18]=[CH:17][C:16]([CH2:19][NH:20][CH2:21][C:22]3[NH:23][CH:24]=[CH:25][N:26]=3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)CC.[CH:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[C:33]([CH:41]=O)[N:32]=1.[C:43]([BH3-])#[N:44].[Na+].[OH-].[Na+]>CO.C(O)(=O)C>[CH2:6]([N:44]([CH2:43][C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12](=[O:27])[C:13]2[CH:14]=[CH:15][C:16]([CH2:19][N:20]([CH2:21][C:22]3[NH:26][CH:25]=[CH:24][N:23]=3)[CH2:41][C:33]3[N:32]=[CH:31][C:40]4[C:35]([CH:34]=3)=[CH:36][CH:37]=[CH:38][CH:39]=4)=[CH:17][CH:18]=2)=[CH:9][CH:10]=1)[CH2:7][CH2:8][CH3:9])[CH2:5][CH3:10]

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 231555Isoquinoline-3-carboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 21084514N-[4-(dipropylamino)phenyl]-4-[(1H-imidazol-2-ylmethylamino)methyl]benzamide

Produkt 1

HCID 10257239N-[4-[(dipropylamino)methyl]phenyl]-4-[[1H-imidazol-2-ylmethyl(3-isoquinolylmethyl)amino]methyl]benzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

The compound (53.9 mg) obtained in Example 47-3 was dissolved in methanol (2.0 ml) and then added with the compound (20.2 mg) obtained in Example 47-1 and sodium cyanoborohydride (12.8 mg). Then, the solution was adjusted to pH 5 with acetic acid and then stirred at room temperature for 14 hours. After completion of the reaction, a 1 mol/l sodium hydroxide aqueous solution was added to the reaction solution, followed by separation/extraction with chloroform. 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 then treated with hydrochloric acid, thereby obtaining hydrochloride (10.1 mg) of the subject compound as a white solid.

Aufarbeitung

  1. customAfter completion of the reaction
  2. extractionfollowed by separation/extraction with chloroform
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  4. distillationthe solvent was then distilled off
  5. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)
  6. additiontreated with hydrochloric acid

Quellen und Nachweise

ORD-Eintrag
ord-3f579dad1bdb415daf6b719d9339c442
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07833991B2

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