Diisopropylethylamine → HCID 69034229, compound

HRID 1046768Notes

Reaction equation

HRID 1046768 reaction equation
[NH2:1][CH:2]([C:4]1[N:5]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:6](=[O:15])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][C:8]=2[CH3:14])[CH3:3].Cl[C:23]1[N:31]=[C:30]([F:32])[N:29]=[C:28]2[C:24]=1[N:25]=[CH:26][N:27]2C1CCCCO1.CCN(C(C)C)C(C)C.[F:48][C:49]1[N:57]=[C:56]2[C:52]([N:53]=[C:54]([NH:64][CH:65]([C:67]3[N:68]([C:79]4[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=4)[C:69](=[O:78])[C:70]4[C:75]([CH:76]=3)=[CH:74][CH:73]=[CH:72][C:71]=4[CH3:77])[CH3:66])[N:55]2[CH:58]2[CH2:63][CH2:62][CH2:61][CH2:60][O:59]2)=[CH:51][N:50]=1>CCCCO>[F:32][C:30]1[N:29]=[C:28]2[C:24]([N:25]=[CH:26][NH:27]2)=[C:23]([NH:1][C@H:2]([C:4]2[N:5]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:6](=[O:15])[C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][C:8]=3[CH3:14])[CH3:3])[N:31]=1.[F:48][C:49]1[N:57]=[C:56]2[C:52]([N:53]=[C:54]([NH:64][CH:65]([C:67]3[N:68]([C:79]4[CH:80]=[CH:81][CH:82]=[CH:83][CH:84]=4)[C:69](=[O:78])[C:70]4[C:75]([CH:76]=3)=[CH:74][CH:73]=[CH:72][C:71]=4[CH3:77])[CH3:66])[N:55]2[CH:58]2[CH2:63][CH2:62][CH2:61][CH2:60][O:59]2)=[CH:51][N:50]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 24762180HCID 24762180, compound2×HCID 69033205HCID 69033205, compoundHCID 69034229HCID 69034229, compound

Product 2

HCID 69034229HCID 69034229, compoundYield 47%HCID 178423764HCID 178423764, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

3-(1-Aminoethyl)-8-methyl-2-phenylisoquinolin-1(2H)-one (200 mg, 0.72 mol), 6-chloro-2-fluoro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (compound 5202) (369 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-fluoro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-ylamino)ethyl)-8-methyl-2-phenylisoquinolin-1(2H)-one (compound 5203) (167 mg, 47% yield) as a white solid.

Workup

  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)

Sources & evidence

ORD record
ord-d104e487c94c4047b3abbf6115c97b6f
Source dataset
uspto-grants-2013_10
Patent number
US08569323B2

Reaction notes

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