Water → HCID 68109074, Verbindung

HRID 1809711Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1809711
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[N:12][C:13](Cl)=[N:14][CH:15]=3)[N:10]([C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.CCN(C(C)C)C(C)C.[C:46]([O:50][C:51](=[O:60])[NH:52][CH:53]1[CH2:58][CH2:57][CH:56]([NH2:59])[CH2:55][CH2:54]1)([CH3:49])([CH3:48])[CH3:47].O>CN(C=O)C>[C:46]([O:50][C:51](=[O:60])[NH:52][CH:53]1[CH2:54][CH2:55][CH:56]([NH:59][C:13]2[N:12]=[C:11]3[N:10]([C:18]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:9]=[C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=4)[C:16]3=[CH:15][N:14]=2)[CH2:57][CH2:58]1)([CH3:49])([CH3:47])[CH3:48]

Komponenten

6

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 2756050Cis tert-Butyl 4-aminocyclohexylcarbamateHCID 866679653-(3-bromo-phenyl)-6-chloro-1-trityl-1H-pyrazolo[3,4-d]pyrimidine

Produkt 1

HCID 68109074HCID 68109074, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of 3-(3-bromo-phenyl)-6-chloro-1-trityl-1H-pyrazolo[3,4-d]pyrimidine (from Example 42 supra) (1.10 g, 2.0 mmol) in DMF (20 mL) was add DIPEA (0.39 g, 2.8 mmol) and (4-amino-cyclohexyl)-carbamic acid tert-butyl ester (0.60 g, 2.8 mmol). This mixture was stirred at 120° C. for 12 hours. After cooling to room temperature, the reaction mixture was poured into water (100 mL) and the resulting precipitate was collected by filtration. The obtained yellow solid was purified by chromatography (silica gel, MeOH:dichloromethane, 1:100) to give a light solid which was washed with ether (4 mL) to give {4-[3-(3-bromo-phenyl)-1-trityl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester as a white solid. (Yield 730 mg, 50.1%).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. filtrationthe resulting precipitate was collected by filtration
  3. customThe obtained yellow solid was purified by chromatography (silica gel, MeOH:dichloromethane, 1:100)
  4. customto give a light solid which
  5. washwas washed with ether (4 mL)

Quellen und Nachweise

ORD-Eintrag
ord-5c3c630a88ac444186d488b5079ecd7d
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362023B2

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