Dicyclohexylcarbodiimide → 4-{[bis(1H-imidazol-2-ylmethyl)-amino]-methyl}-N-(3-dipropylaminopropyl)-benzamide

HRID 1173856Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1173856
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=1)[CH2:8][C:9]1[NH:10][CH:11]=[CH:12][N:13]=1.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.[CH2:49]([N:52]([CH2:57][CH2:58][CH3:59])[CH2:53][CH2:54][CH2:55][NH2:56])[CH2:50][CH3:51]>CN(C=O)C>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]([NH:56][CH2:55][CH2:54][CH2:53][N:52]([CH2:57][CH2:58][CH3:59])[CH2:49][CH2:50][CH3:51])=[O:21])=[CH:22][CH:23]=1)[CH2:8][C:9]1[NH:13][CH:12]=[CH:11][N:10]=1

Komponenten

6

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 239005n,n-Dipropylpropane-1,3-diamineHCID 669419114-[N,N-bis-(imidazol-2-ylmethyl)aminomethyl]-benzoic Acid

Produkt 1

HCID 103438074-{[bis(1H-imidazol-2-ylmethyl)-amino]-methyl}-N-(3-dipropylaminopropyl)-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The compound (190 mg) obtained in Example 2-2 was dissolved in DMF (3.0 ml) and added with DCC (189 mg), HOBt (124 mg), and the compound (96.9 mg) obtained in Example 22-3, followed by stirring overnight at room temperature. After completion of the reaction, the solvent was distilled off and the residue was then dissolved in chloroform, followed by separating the solution into layers by the addition of 1 mol/l hydrochloric acid. The aqueous layer was made basic with a 1 mol/l sodium hydroxide aqueous solution. Then, the solution was subjected to extraction with chloroform. The extract was washed with saturated saline solution and the organic layer was then dried with anhydrous sodium sulfate. The solvent was distilled off. Subsequently, the residue was treated with hydrochloric acid and then purified through silica gel column chromatography (chloroform/methanol/water), thereby obtaining hydrochloride (84.8 mg) of the subject compound as a white solid.

Aufarbeitung

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. dissolutionthe residue was then dissolved in chloroform
  4. customby separating the solution into layers
  5. additionby the addition of 1 mol/l hydrochloric acid
  6. extractionThen, the solution was subjected to extraction with chloroform
  7. washThe extract was washed with saturated saline solution
  8. dry with materialthe organic layer was then dried with anhydrous sodium sulfate
  9. distillationThe solvent was distilled off
  10. additionSubsequently, the residue was treated with hydrochloric acid
  11. custompurified through silica gel column chromatography (chloroform/methanol/water)

Quellen und Nachweise

ORD-Eintrag
ord-ebb67e245ec34811952db654e8ce3b51
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07833991B2

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