N,N'-Dimethylethylenediamine → HCID 86676697, compound

HRID 1775098Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:10](I)=[N:9][N:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[C:5]2=[CH:6][N:7]=1.[C:18]([N:21]1[CH2:25][CH2:24][NH:23][C:22]1=[O:26])(=[O:20])[CH3:19].CNCCNC.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>[Cu]I>[C:18]([N:21]1[CH2:25][CH2:24][N:23]([C:10]2[C:4]3[C:5](=[CH:6][N:7]=[C:2]([Br:1])[CH:3]=3)[N:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[N:9]=2)[C:22]1=[O:26])(=[O:20])[CH3:19]

Participants

Conditions

Temperature: 75 °C

Procedure

A solution containing 5-bromo-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine (1.00 g, 2.45 mmol), 1-acetylimidazolidin-2-one (0.3768 g, 2.941 mmol), N,N′-Dimethylethylenediamine (0.528 mL, 4.90 mmol), Copper(I) iodide (0.467 g, 2.45 mmol) and Potassium carbonate (0.4064 g, 2.941 mmol) in 1,4-Dioxane (40.0 mL, 512 mmol) was stirred at 75° C. for 2 h. The reaction was filtered thru celite and concentrated. The crude product purified by Isco column (1% MeOH/EtOAc/Hep eluted at 55% EtOAc) to give 1-acetyl-3-(5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)imidazolidin-2-one (620 mg, 62% yield). ESI MS m/z=408.1 (M+1).

Workup

filtrationThe reaction was filtered thru celite
concentrationconcentrated
customThe crude product purified by Isco column (1% MeOH/EtOAc/Hep eluted at 55% EtOAc)

Sources & evidence

ORD record: ord-158d2a547644476e8b5a133c7a9b5ab7
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260425B2

Reaction notes

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