Piperazine → Cgp-74588

HRID 970310

Reaktionsgleichung

Reaktionsgleichung von HRID 970310
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[CH2:8][C:9]1[CH:37]=[CH:36][C:12]([C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([NH:23][C:24]3[N:29]=[C:28]([C:30]4[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=4)[CH:27]=[CH:26][N:25]=3)[CH:17]=2)=[O:14])=[CH:11][CH:10]=1>C(O)C.O>[CH3:22][C:19]1[CH:20]=[CH:21][C:16]([NH:15][C:13](=[O:14])[C:12]2[CH:11]=[CH:10][C:9]([CH2:8][N:1]3[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]3)=[CH:37][CH:36]=2)=[CH:17][C:18]=1[NH:23][C:24]1[N:29]=[C:28]([C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)[CH:27]=[CH:26][N:25]=1

Komponenten

5

Edukt 2

HCID 4837PiperazineHCID 101810754-(Chloromethyl)-N-(4-methyl-3-((4-(3-pyridinyl)-2-pyrimidinyl)amino)phenyl)benzamide

Produkt 1

HCID 9869737Cgp-74588

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

25.8 g (300 mmol) of piperazine are suspended in a mixture of 25 ml of ethanol and 25 ml of water. After almost a clear solution has formed, 12.9 g (30 mmol) of 4-chloromethyl-N-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-benzamide are added step by step. The yellow solution is boiled under reflux for 14 hours, cooled to room temperature and filtered over Celite. 100 ml of water is added to the solution, the ethanol is evaporated under vacuum and 30 ml of 1N NaOH is added, leading to crystallization of the product. Drying at 50 mbar and 60° C. yields N-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-4-piperazin-1-ylmethyl-benzamide; Rf=0.15 (methylene chloride:ethyl acetate:methanol:conc. aqueous ammonium hydroxide solution=60:10:30:2); tR (HPLC)2) 14.6 min.

Aufarbeitung

  1. customAfter almost a clear solution has formed
  2. temperatureunder reflux for 14 hours
  3. filtrationfiltered over Celite
  4. addition100 ml of water is added to the solution
  5. customthe ethanol is evaporated under vacuum and 30 ml of 1N NaOH
  6. additionis added
  7. customleading to crystallization of the product
  8. customDrying at 50 mbar and 60° C.

Quellen und Nachweise

ORD-Eintrag
ord-bda9621ad94543d4bb433a1bdaebf06b
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07312216B2

Verknüpfte Notizen

Wird geladen…