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Triethylamine → (3-{3-[1-(4-Amino-3-bromo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl}azetidin-1-yl)acetonitrile

HRID 1499783
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1499783
[NH:1]1[CH2:4][CH:3]([C:5]2[C:6]([O:26][CH3:27])=[C:7]([CH:13]([N:15]3[C:19]4=[N:20][CH:21]=[N:22][C:23]([NH2:24])=[C:18]4[C:17]([Br:25])=[N:16]3)[CH3:14])[CH:8]=[C:9]([Cl:12])[C:10]=2[CH3:11])[CH2:2]1.[CH2:28]([N:30](CC)CC)[CH3:29].BrCC#N>C(#N)C.CN(C=O)C>[NH2:24][C:23]1[N:22]=[CH:21][N:20]=[C:19]2[N:15]([CH:13]([C:7]3[C:6]([O:26][CH3:27])=[C:5]([CH:3]4[CH2:4][N:1]([CH2:29][C:28]#[N:30])[CH2:2]4)[C:10]([CH3:11])=[C:9]([Cl:12])[CH:8]=3)[CH3:14])[N:16]=[C:17]([Br:25])[C:18]=12
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Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 11534BromoacetonitrileHCID 866777091-[1-(3-Azetidin-3-yl-5-chloro-2-methoxy-4-methylphenyl)ethyl]-3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Produkt 1

HCID 86677710(3-{3-[1-(4-Amino-3-bromo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl}azetidin-1-yl)acetonitrileAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228
Dimethylformamide
Katalysator
HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a mixture of 1-[1-(3-azetidin-3-yl-5-chloro-2-methoxy-4-methylphenyl)ethyl]-3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (100 mg, 0.2 mmol) and triethylamine (37 μL, 0.27 mmol) in acetonitrile (3 mL) was added bromoacetonitrile (19 μL, 0.27 mmol). The resulting mixture was stirred at room temp. After an hour, the reaction mixture was still cloudy with not all of the material in solution. Several drops of DMF were added which allowed for a clear solution. The mixture was stirred overnight at room temperature and then most of the solvents were evaporated. The resulting residue was purified on silica gel (eluted with 0-10% MeOH in dichloromethane) to give 29 mg (30%) of the desired product. LCMS calculated for C20H22BrClN7O (M+H)+: m/z=490.1; Found: 490.1.

Aufarbeitung

  1. waitAfter an hour
  2. stirringThe mixture was stirred overnight at room temperature
  3. custommost of the solvents were evaporated
  4. customThe resulting residue was purified on silica gel (eluted with 0-10% MeOH in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-59c8863fd65d457dbd58c956f278de6b
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09199982B2

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