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

HRID 1502503

反応式

HRID 1502503 の反応式
N[C@H](C1N(C2CC2)C(=O)C2C(C=1)=CC=CC=2C)C.ClC1N=CN=C2C=1N=CN2C1CCCCO1.CCN(C(C)C)C(C)C.[CH:44]1([N:47]2[C:56]([C@@H:57]([NH:59][C:60]3[N:68]=[CH:67][N:66]=[C:65]4[C:61]=3[N:62]=[CH:63][N:64]4[CH:69]3[CH2:74][CH2:73][CH2:72][CH2:71][O:70]3)[CH3:58])=[CH:55][C:54]3[C:49](=[C:50]([CH3:75])[CH:51]=[CH:52][CH:53]=3)[C:48]2=[O:76])[CH2:46][CH2:45]1>CCCCO>[N:68]1[C:60]([NH:59][C@H:57]([C:56]2[N:47]([CH:44]3[CH2:46][CH2:45]3)[C:48](=[O:76])[C:49]3[C:54]([CH:55]=2)=[CH:53][CH:52]=[CH:51][C:50]=3[CH3:75])[CH3:58])=[C:61]2[C:65]([NH:64][CH:63]=[N:62]2)=[N:66][CH:67]=1.[CH:44]1([N:47]2[C:56]([C@@H:57]([NH:59][C:60]3[N:68]=[CH:67][N:66]=[C:65]4[C:61]=3[N:62]=[CH:63][N:64]4[CH:69]3[CH2:74][CH2:73][CH2:72][CH2:71][O:70]3)[CH3:58])=[CH:55][C:54]3[C:49](=[C:50]([CH3:75])[CH:51]=[CH:52][CH:53]=3)[C:48]2=[O:76])[CH2:45][CH2:46]1

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 977406-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purineHCID 58008913(S)-3-(1-Aminoethyl)-2-cyclopropyl-8-methylisoquinolin-1(2H)-one2 回HCID 580089832-cyclopropyl-8-methyl-3-((1S)-1-(9-(tetrahydro-2H-Pyran-2-yl)-9H-purin-6-ylamino)ethyl)isoquinolin-1(2H)-one

生成物 2

HCID 580089832-cyclopropyl-8-methyl-3-((1S)-1-(9-(tetrahydro-2H-Pyran-2-yl)-9H-purin-6-ylamino)ethyl)isoquinolin-1(2H)-one収率 65%HCID 178423765(S)-3-(1-(9H-purin-6-ylamino)ethyl)-2-cyclopropyl-8-methylisoquinolin-1(2H)-one

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

実験手順

(S)-3-(1-Aminoethyl)-2-cyclopropyl-8-methylisoquinolin-1(2H)-one (242 mg, 1 mmol) (compound 5003), 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 the residue was purified by flash column chromatography on silica gel (eluting with 30% to 50% Hex/EA) to afford the desired product, 2-cyclopropyl-8-methyl-3-((1S)-1-(9-(tetrahydro-2H-Pyran-2-yl)-9H-purin-6-ylamino)ethyl)isoquinolin-1(2H)-one (compound 5004) (288 mg, 65% yield) as a white solid.

後処理

  1. temperatureat reflux for 16 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was purified 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-086cba3de83243bdac7df65a1d5005d7
出典データセット
uspto-grants-2015_12
特許番号
US09206182B2

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