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

HRID 1627216

반응식

HRID 1627216 반응식
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

참가 물질

7

반응물 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)-one2회

생성물 2

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

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8f444f6bf09a4d5691ca2783873cb94e
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785456B2

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