Piperazine → 6-Chloro-7-(4-hydroxypiperidin-1-yl)-2-piperazin-1-yl-4-pyrrolidin-1-yl-pteridine

HRID 330851Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 330851
[N:1]1([C:6]2[C:15]3[C:10](=[N:11][C:12](Cl)=[C:13]([Cl:16])[N:14]=3)[N:9]=[C:8](Cl)[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:19][CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(N(C(C)C)CC)(C)C.[NH:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1>O1CCOCC1>[Cl:16][C:13]1[N:14]=[C:15]2[C:10](=[N:11][C:12]=1[N:23]1[CH2:24][CH2:25][CH:20]([OH:19])[CH2:21][CH2:22]1)[N:9]=[C:8]([N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)[N:7]=[C:6]2[N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

6

Edukt 4

HCID 4837PiperazineHCID 79341Piperidin-4-olHCID 81531DiisopropylethylamineHCID 137998844-Pyrrolidin-1-yl-2,6,7-trichloropteridine

Produkt 1

HCID 866167636-Chloro-7-(4-hydroxypiperidin-1-yl)-2-piperazin-1-yl-4-pyrrolidin-1-yl-pteridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

a)+b) 80 mg (0.26 mmol) 4-pyrrolidin-1-yl-2,6,7-trichloro-pteridine are dissolved in 5 ml dioxane and combined with 29 mg (0.29 mmol) 4-hydroxypiperidin and 49 μl (0.37 mmol) diisopropylethylamine. The mixture is stirred for approx. 16 h at 40° C. The reaction mixture is then slowly added dropwise to a solution of 113 mg (1 mmol) piperazine in 15 ml dioxane at a temperature of 80° C. The mixture is stirred for approx. 16 h at 80° C., cooled to ambient temperature and then poured onto ice water. It is extracted with dichloromethane, the organic phase is dried on sodium sulphate and the solvent is eliminated in vacuo. The residue is taken up in some dichloromethane and combined with petroleum ether, the precipitate formed is suction filtered. Yield 58 mg (53% of theoretical).

Aufarbeitung

  1. stirringThe mixture is stirred for approx. 16 h at 80° C.
  2. temperaturecooled to ambient temperature
  3. additionpoured onto ice water
  4. extractionIt is extracted with dichloromethane
  5. customthe organic phase is dried on sodium sulphate
  6. customthe precipitate formed
  7. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-c7ac017b0edf477ea885dc502f2b3938
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877756B2

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