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

HRID 217133

Reaktionsgleichung

Reaktionsgleichung von HRID 217133
N[C@H](C1N(C2C=CC=CC=2)C(=O)C2C(C=1)=CC=CC=2C)C.ClC1N=C2C(N=CN2C2CCCCO2)=C(Cl)N=1.CCN(C(C)C)C(C)C.[Cl:48][C:49]1[N:57]=[C:56]2[C:52]([N:53]=[CH:54][N:55]2[CH:58]2[CH2:63][CH2:62][CH2:61][CH2:60][O:59]2)=[C:51]([NH:64][CH:65]([C:67]2[N:68]([C:79]3[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=3)[C:69](=[O:78])[C:70]3[C:75]([CH:76]=2)=[CH:74][CH:73]=[CH:72][C:71]=3[CH3:77])[CH3:66])[N:50]=1>CCCCO>[Cl:48][C:49]1[N:57]=[C:56]2[C:52]([N:53]=[CH:54][NH:55]2)=[C:51]([NH:64][C@H:65]([C:67]2[N:68]([C:79]3[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=3)[C:69](=[O:78])[C:70]3[C:75]([CH:76]=2)=[CH:74][CH:73]=[CH:72][C:71]=3[CH3:77])[CH3:66])[N:50]=1.[Cl:48][C:49]1[N:57]=[C:56]2[C:52]([N:53]=[CH:54][N:55]2[CH:58]2[CH2:63][CH2:62][CH2:61][CH2:60][O:59]2)=[C:51]([NH:64][CH:65]([C:67]2[N:68]([C:79]3[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=3)[C:69](=[O:78])[C:70]3[C:75]([CH:76]=2)=[CH:74][CH:73]=[CH:72][C:71]=3[CH3:77])[CH3:66])[N:50]=1

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 2702652,6-Dichloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine2×HCID 58008747(S)-3-(1-aminoethyl)-8-methyl-2-phenylisoquinolin-1(2H)-one2×HCID 866371703-(1-(2-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-ylamino)ethyl)-8-methyl-2-phenylisoquinolin-1(2H)-one

Produkt 2

HCID 866371703-(1-(2-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-ylamino)ethyl)-8-methyl-2-phenylisoquinolin-1(2H)-oneAusbeute 46 %HCID 178423763HCID 178423763, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

3-(1-Aminoethyl)-8-methyl-2-phenylisoquinolin-1(2H)-one (compound 4704) (200 mg, 0.72 mol), 2,6-dichloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (compound 5302) (393 mg, 1.44 mmol) and DIPEA (279 mg, 2.16 mmol) were dissolved in n-BuOH (20 mL) in a sealed tube, and the resulting mixture was stirred at 120° C. for 16 h. The reaction mixture was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (eluting with 30% to 50% Hex/EA) to afford the desired product, 3-(1-(2-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-ylamino)ethyl)-8-methyl-2-phenylisoquinolin-1(2H)-one (compound 5303) (172 mg, 46% yield) as a white solid.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by flash column chromatography on silica gel (eluting with 30% to 50% Hex/EA)

Quellen und Nachweise

ORD-Eintrag
ord-3911d7d9ac0a417a9ba3264773ddfe51
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193182B2

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