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

HRID 1046764노트

반응식

HRID 1046764 반응식
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

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 977406-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purineHCID 58008913(S)-3-(1-Aminoethyl)-2-cyclopropyl-8-methylisoquinolin-1(2H)-one2회HCID 580089832-cyclopropyl-8-methyl-3-((1S)-1-(9-(tetrahydro-2H-Pyran-2-yl)-9H-purin-6-ylamino)ethyl)isoquinolin-1(2H)-one

생성물 2

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

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

(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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ecc55cc53b0940eeb10c8c46a122610c
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569323B2

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