Diisopropylethylamine → HCID 69034229, compound

HRID 217131Notes

Reaction equation

HRID 217131 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].CCN(C(C)C)C(C)C.[F:31][C:32]1[N:40]=[C:39]2[C:35]([N:36]=[C:37]([NH:47][CH:48]([C:50]3[N:51]([C:62]4[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=4)[C:52](=[O:61])[C:53]4[C:58]([CH:59]=3)=[CH:57][CH:56]=[CH:55][C:54]=4[CH3:60])[CH3:49])[N:38]2[CH:41]2[CH2:46][CH2:45][CH2:44][CH2:43][O:42]2)=[CH:34][N:33]=1>CCCCO>[F:31][C:32]1[N:40]=[C:39]2[C:35]([N:36]=[CH:37][NH:38]2)=[C:34]([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:33]=1.[F:31][C:32]1[N:40]=[C:39]2[C:35]([N:36]=[C:37]([NH:47][CH:48]([C:50]3[N:51]([C:62]4[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=4)[C:52](=[O:61])[C:53]4[C:58]([CH:59]=3)=[CH:57][CH:56]=[CH:55][C:54]=4[CH3:60])[CH3:49])[N:38]2[CH:41]2[CH2:46][CH2:45][CH2:44][CH2:43][O:42]2)=[CH:34][N:33]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 69033205HCID 69033205, compound2×HCID 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-2fluoro-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-073d735b58de46248172dd07a7faa31c
Source dataset
uspto-grants-2012_06
Patent number
US08193182B2

Reaction notes

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