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Sodium hydride → HCID 178476566, Verbindung

HRID 432219
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 432219
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:18]3[CH2:23][CH2:22][CH:21]([N:24]4[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]4)[CH2:20][CH2:19]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)[C:3]=12.[H-].[Na+].F[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[N+:40]([O-:42])=[O:41]>O1CCOCC1>[C:14]([OH:17])(=[O:41])[CH3:15].[C:14]([OH:17])(=[O:41])[CH3:15].[CH3:30][N:27]1[CH2:26][CH2:25][N:24]([C@@H:21]2[CH2:22][CH2:23][C@H:18]([N:8]3[C:4]4=[N:5][CH:6]=[N:7][C:2]([NH2:1])=[C:3]4[C:10]([C:11]4[CH:16]=[CH:15][C:14]([O:17][C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=5[N+:40]([O-:42])=[O:41])=[CH:13][CH:12]=4)=[N:9]3)[CH2:19][CH2:20]2)[CH2:29][CH2:28]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24758Sodium hydride2×HCID 738951-Fluoro-2-nitrobenzene2×HCID 1358414224-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenol

Produkt 1

HCID 178476566HCID 178476566, VerbindungAusbeute 26,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31275
1,4-Dioxane
Lösungsmittel

Versuchsvorschrift

A mixture of 4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenol (0.200 g, 0.491 mmol, 1 equiv) and 60% sodium hydride (0.020 g, 0.49 mmol, 1 equiv) in dioxane (4.9 mL) was stirred at ambient temperature for 20 minutes. 2-Fluoronitrobenzene (0.06 mL, 0.6 mmol, 1.1 equiv) was added and the reaction mixture was heated at 100° C. for 3 h. Additional sodium hydride (0.010 g, 0.24 mmol, 0.5 equiv) and 2-fluoronitrobenzene (0.02 mL, 0.2 mmol, 0.4 equiv) were added and the reaction mixture was heated at 100° C. for 3 h. The reaction mixture was allowed to cool to room temperature and the resulting solid was removed by filtration with the aid of CH2Cl2 (10 mL) and EtOAc (10 mL). The filtrate was concentrated to afford a yellow semi-solid which was purified by preparative RP-HPLC (Rainin C18, 8 μm, 300 Å, 25 cm; 10%-60% acetonitrile-0.1M ammonium acetate over 20 min, 21 mL/min). The acetonitrile was removed in vacuo and the aqueous mixture was lyopholyzed to afford cis-1-[4-(4-methylpiperazino)cyclohexyl]-3-[4-(2-nitrophenoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine diacetate salt as a white solid (0.023 g, 0.043 mmol): 1H NMR (d6 DMSO, 400 MHz): δ H 8.23 (1H, s), 8.10 (1H, d, J=8.2 Hz), 7.68-7.73 (3H, m), 7.33-7.40 (1H, m), 7.31 (1H, d, J=7.3 Hz), 7.24 (2H, d, J=8.7 Hz), 4.76-4.82 (1H, m), 2.26-2.51 (1H, m), 2.24 (3H, s), 2.17-2.21 (2H, m), 2.05 (6H, s), 1.56-1.71 (4H, m); RP-HPLC (Delta Pak C18, 5 μm, 300 Å, 15 cm; 5%-85% acetonitrile-0.1M ammonium acetate over 20 min, 1 mL/min) Rt 13.09 min.

Aufarbeitung

  1. temperaturethe reaction mixture was heated at 100° C. for 3 h
  2. temperaturethe reaction mixture was heated at 100° C. for 3 h
  3. temperatureto cool to room temperature
  4. customthe resulting solid was removed by filtration with the aid of CH2Cl2 (10 mL) and EtOAc (10 mL)
  5. concentrationThe filtrate was concentrated
  6. customto afford a yellow semi-solid which
  7. customwas purified by preparative RP-HPLC (Rainin C18, 8 μm, 300 Å, 25 cm; 10%-60% acetonitrile-0.1M ammonium acetate over 20 min, 21 mL/min)
  8. customThe acetonitrile was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-830eb6c2d6064750af36ccf0d301f629
Quelldatensatz
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06660744B1

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