HCID 18704982, Verbindung → HCID 178523915, Verbindung

HRID 376331Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 376331
CS[C:3]([N:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH2:15][CH2:14]1)=[N:4][C:5](=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Br:25][C:26]1[CH:43]=[CH:42][C:29]([CH2:30][N:31]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=2)[CH2:32][CH2:33][CH2:34][NH2:35])=[CH:28][CH:27]=1>N1C=CC=CC=1>[Br:25][C:26]1[CH:43]=[CH:42][C:29]([CH2:30][N:31]([CH2:32][CH2:33][CH2:34][NH:35][C:3]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[CH2:15][CH2:14]2)=[N:4][C:5](=[O:12])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=2)=[CH:28][CH:27]=1

Komponenten

4

Edukt 2

HCID 18704982HCID 18704982, VerbindungHCID 22118499HCID 22118499, Verbindung

Produkt 1

HCID 178523915HCID 178523915, VerbindungAusbeute 56,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a mixture of N-[methylsulfanyl-(4-(pyridin-2-yl)piperazin-1-yl)methylene]-benzamide (2.9 g, 8.52 mmol) in pyridine (50 ml) was added N1-(4-bromobenzyl)-N1-(pyridin-2-yl)-propane-1,3-diamine (3 g, 9.37 mmol) and the reaction mixture was heated at reflux for 18 h. The volatiles were evaporated in vacuo and the residue dissolved in dichloromethane (100 ml) and evaporated in vacuo. The residue was purified by column chromatography on silica gel (600 ml) using first a mixture of ethyl acetate/triethylamine 95:5 (1 l) followed by a mixture of ethyl acetate/methanol/triethylamine 90:5:5 as eluents affording 2.95 g of N-[[3-[N-(4-bromo-benzyl)-N-(pyridin-2-yl)amino]propylamino]-(4-pyridin-2-yl-piperazin-1-yl) methylene]benzamide as a foam.

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 18 h
  3. customThe volatiles were evaporated in vacuo
  4. dissolutionthe residue dissolved in dichloromethane (100 ml)
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (600 ml)
  7. additiona mixture of ethyl acetate/triethylamine 95:5 (1 l)
  8. additionfollowed by a mixture of ethyl acetate/methanol/triethylamine 90:5:5 as eluents

Quellen und Nachweise

ORD-Eintrag
ord-a4c7dcd9268a46e5b52a47034cb3f5fa
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06020349

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