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

HRID 1046763

反応式

HRID 1046763 の反応式
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

参加物

7

反応物 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 回

生成物 2

HCID 580085588-methyl-2-phenyl-3-((1S)-1-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-ylamino)ethyl)-isoquinolin-1(2H)-one収率 60%HCID 178423766HCID 178423766、化合物

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-7fc6b7c7ec354bfc981ebd91f0e95363
出典データセット
uspto-grants-2013_10
特許番号
US08569323B2

関連ノート

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