Styrene Oxide → HCID 178488201, Verbindung

HRID 897610

Reaktionsgleichung

Reaktionsgleichung von HRID 897610
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[N:14][C:15]=3[NH2:17])[N:10]([C@H:18]3[CH2:23][CH2:22][C@@H:21]([N:24]4[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]4)[CH2:20][CH2:19]3)[N:9]=2)=[CH:4][C:3]=1[O:31][CH3:32].[CH2:33]1[O:41][CH:34]1[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(O)(C)C>[NH2:17][C:15]1[N:14]=[CH:13][N:12]=[C:11]2[N:10]([C@H:18]3[CH2:23][CH2:22][C@@H:21]([N:24]4[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]4)[CH2:20][CH2:19]3)[N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][CH:34]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[CH2:33][OH:41])=[C:3]([O:31][CH3:32])[CH:4]=3)[C:16]=12

Komponenten

4

Edukt 2

HCID 7276Styrene OxideHCID 178488197HCID 178488197, Verbindung

Produkt 1

HCID 178488201HCID 178488201, VerbindungAusbeute 5,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

Cis-3-(4-amino-3-methoxyphenyl)-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.075 g, 0.000172 mol) and styrene oxide (0.029 g, 0.000172 mol) were dissolved in isopropanol (3 mL) and the resulting mixture was heated at reflux for 24 hours. The solvent was removed and the residue purified by preparative HPLC (Hypersil C18, 8 μm, 25 cm; 10-60% acetonitrile-0.1M ammonium acetate over 25 min, 21 mL/min) to yield cis-2-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyanilino)-2-phenyl-1-ethanol (0.005 g, 0.0000089 mol) as an off-white solid.

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 24 hours
  3. customThe solvent was removed
  4. customthe residue purified by preparative HPLC (Hypersil C18, 8 μm, 25 cm; 10-60% acetonitrile-0.1M ammonium acetate over 25 min, 21 mL/min)

Quellen und Nachweise

ORD-Eintrag
ord-9f059e4f1e9b463992e768440d0ffb5e
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06921763B2

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