Diisopropylethylamine → 8-methyl-2-phenyl-3-((1S)-1-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-ylamino)ethyl)-isoquinolin-1(2H)-one

HRID 1506102

Reaktionsgleichung

Reaktionsgleichung von HRID 1506102
N[C@H](C1N(C2C=CC=CC=2)C(=O)C2C(C=1)=CC=CC=2C)C.ClC1N=CN=C2C=1N=CN2C1CCCCO1.CCN(C(C)C)C(C)C.[CH3:47][C:48]1[CH:49]=[CH:50][CH:51]=[C:52]2[C:57]=1[C:56](=[O:58])[N:55]([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[C:54]([C@@H:65]([NH:67][C:68]1[N:76]=[CH:75][N:74]=[C:73]3[C:69]=1[N:70]=[CH:71][N:72]3[CH:77]1[CH2:82][CH2:81][CH2:80][CH2:79][O:78]1)[CH3:66])=[CH:53]2>CCCCO>[N:76]1[C:68]([NH:67][C@H:65]([C:54]2[N:55]([C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=3)[C:56](=[O:58])[C:57]3[C:52]([CH:53]=2)=[CH:51][CH:50]=[CH:49][C:48]=3[CH3:47])[CH3:66])=[C:69]2[C:73]([NH:72][CH:71]=[N:70]2)=[N:74][CH:75]=1.[CH3:47][C:48]1[CH:49]=[CH:50][CH:51]=[C:52]2[C:57]=1[C:56](=[O:58])[N:55]([C:59]1[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=1)[C:54]([C@@H:65]([NH:67][C:68]1[N:76]=[CH:75][N:74]=[C:73]3[C:69]=1[N:70]=[CH:71][N:72]3[CH:77]1[CH2:82][CH2:81][CH2:80][CH2:79][O:78]1)[CH3:66])=[CH:53]2

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 977406-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purineHCID 580085588-methyl-2-phenyl-3-((1S)-1-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-ylamino)ethyl)-isoquinolin-1(2H)-oneHCID 58008747(S)-3-(1-aminoethyl)-8-methyl-2-phenylisoquinolin-1(2H)-one2×

Produkt 2

HCID 580085588-methyl-2-phenyl-3-((1S)-1-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-ylamino)ethyl)-isoquinolin-1(2H)-oneAusbeute 60 %HCID 178423766HCID 178423766, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

3-(1-Aminoethyl)-8-methyl-2-phenylisoquinolin-1(2H)-one (compound 4704) (200 mg, 0.72 mmol), 6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (344 mg, 1.44 mmol) and DIPEA (279 mg, 2.16 mmol) were dissolved in n-BuOH (20 ml), and the resulting mixture was stirred at reflux for 16 h. The reaction mixture was concentrated in vacuo and purified by flash column chromatography on silica gel (eluting with 30% to 50% Hex/EA) to afford the desired product, 8-methyl-2-phenyl-3-((1S)-1-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-ylamino)ethyl)isoquinolin-1(2H)-one (compound 4901) (207 mg, 60% yield) as a white solid.

Aufarbeitung

  1. temperatureat reflux for 16 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompurified by flash column chromatography on silica gel (eluting with 30% to 50% Hex/EA)

Quellen und Nachweise

ORD-Eintrag
ord-731d35d4bd3f44538509fa4784701634
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216982B2

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