Acetic Acid → N-(4-dipropylamino-butyl)-4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-N-methyl-benzenesulfonamide

HRID 348715

Reaktionsgleichung

Reaktionsgleichung von HRID 348715
[CH2:1]([N:4]([CH2:28][CH2:29][CH3:30])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH3:27])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][NH:20][CH2:21][C:22]2[NH:23][CH:24]=[CH:25][N:26]=2)=[CH:15][CH:14]=1)(=[O:12])=[O:11])[CH2:2][CH3:3].[CH3:31][N:32]1[CH:36]=[CH:35][N:34]=[C:33]1[CH:37]=O.C([BH3-])#N.[Na+].C(O)(=O)C>CO>[CH2:28]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]([CH3:27])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][N:20]([CH2:21][C:22]2[NH:26][CH:25]=[CH:24][N:23]=2)[CH2:37][C:33]2[N:32]([CH3:31])[CH:36]=[CH:35][N:34]=2)=[CH:15][CH:14]=1)(=[O:11])=[O:12])[CH2:29][CH3:30]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 21084503N-(4-dipropylamino-butyl)-4-{[(1H-imidazol-2-ylmethyl)-amino]-methyl}-N-methyl-benzenesulfonamide

Produkt 1

HCID 11950614N-(4-dipropylamino-butyl)-4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-N-methyl-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

The compound (171.8 mg) obtained in Example 112-2 was dissolved in anhydrous methanol (7.0 ml). The solution was added with 1-methyl-2-imidazole carboxaldehyde (65.0 mg) and sodium cyanoborohydride (49.0 mg). Then, the solution was adjusted to pH 5 with acetic acid and then stirred at room temperature for 2 days. After the reaction, the solvent was distilled off. The residue was added with a 1 mol/l sodium hydroxide aqueous solution and extracted with chloroform. The extract was dried with magnesium sulfate, and the solvent was distilled off. Then, the residue was purified through silica gel column chromatography (chloroform/methanol) and treated with hydrochloric acid, thereby obtaining hydrochloride (184.8 mg) of the subject compound as a white solid.

Aufarbeitung

  1. customAfter the reaction
  2. distillationthe solvent was distilled off
  3. additionThe residue was added with a 1 mol/l sodium hydroxide aqueous solution
  4. extractionextracted with chloroform
  5. dry with materialThe extract was dried with magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customThen, the residue was purified through silica gel column chromatography (chloroform/methanol)
  8. additiontreated with hydrochloric acid

Quellen und Nachweise

ORD-Eintrag
ord-f070e0e84f314dd085df8835ee5bbb67
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176227B2

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