2-Dimethylaminopyridine → HCID 86625979, Verbindung

HRID 658271

Reaktionsgleichung

Reaktionsgleichung von HRID 658271
[C:1]1([CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1.CN(C1C=CC=CN=1)C.[CH2:32]([NH:38][C:39]([NH:41][C:42]1[CH:47]=[CH:46][N:45]([CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53]O)[C:44](=[O:55])[N:43]=1)=[O:40])[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>C(Cl)Cl>[CH2:32]([NH:38][C:39](=[O:40])[NH:41][C:42]1[CH:47]=[CH:46][N:45]([CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][O:21][C:20](=[O:22])[CH2:19][CH2:18][CH2:17][C:1]2[C:14]3[C:15]4=[C:16]5[C:11](=[CH:12][CH:13]=3)[CH:10]=[CH:9][CH:8]=[C:7]5[CH:6]=[CH:5][C:4]4=[CH:3][CH:2]=2)[C:44](=[O:55])[N:43]=1)[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Komponenten

5

Edukt 3

HCID 218852-DimethylaminopyridineHCID 769771-Pyrenebutanoic acidHCID 68972726HCID 68972726, Verbindung

Produkt 1

HCID 86625979HCID 86625979, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of pyrene butyric acid (commercially available) (0.05 g, 0.17 mmol) in CH2Cl2 (5 ml) was added at 0° C., dicyclohexylcarboimide (0.044 g, 0.210 mmol) and dimethylaminopyridine (4 mg). The mixture was stirred for 1 h. 1-Hexyl-3-[1-(6-hydroxy-hexyl)-2-oxo-1,2-dihydro-pyrimidinyl]-urea) (J) was then added to the mixture and the solution was stirred at room temperature for 16 h. The solid was filtered off and the filtrate washed with water (2×10 ml) then saturated sodium chloride solution (5 ml). The organic phase was then dried (MgSO4) and the solvent evaporated in vacuo. The crude solid was purified using flash silica gel chromatography using a gradient: 1) (CHCl3) 2) (CHCl3/EtOAc, 5:1) and 3) (CHCl3/EtOAc/Et3N, 5:1:0.2). 4-Pyren-1-yl-butyric acid 6-[4-(3-hexyl-ureido)-2-oxo-2H-pyrimidin-1-yl]-hexyl ester (K) was obtained as a yellow solid (0.025 mg, 23%).

Aufarbeitung

  1. stirringthe solution was stirred at room temperature for 16 h
  2. filtrationThe solid was filtered off
  3. washthe filtrate washed with water (2×10 ml)
  4. dry with materialThe organic phase was then dried (MgSO4)
  5. customthe solvent evaporated in vacuo
  6. customThe crude solid was purified

Quellen und Nachweise

ORD-Eintrag
ord-ba111a3cf5044031ad59db91a39d0426
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076426B2

Verknüpfte Notizen

Wird geladen…