1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1-(2-bromo-5H-pyrrolo[3,2-b]pyrazin-7-yl)-2-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-ylamino)ethanone

HRID 246691Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 246691
[Br:1][C:2]1[N:7]=[C:6]2[C:8]([C:11]([OH:13])=O)=[CH:9][NH:10][C:5]2=[N:4][CH:3]=1.[Si:14]([O:21][CH2:22][C:23]([CH3:26])([NH2:25])[CH3:24])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].[CH3:27]CN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[Br:1][C:2]1[N:7]=[C:6]2[C:8]([C:11](=[O:13])[CH2:27][NH:25][C:23]([CH3:26])([CH3:24])[CH2:22][O:21][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])=[CH:9][NH:10][C:5]2=[N:4][CH:3]=1

Komponenten

8

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 148067402-tert-Butyldimethylsilyloxy-1,1-dimethylethylamineHCID 866778972-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

Produkt 1

HCID 866780031-(2-bromo-5H-pyrrolo[3,2-b]pyrazin-7-yl)-2-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-ylamino)ethanoneAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

A mixture of 2-bromo-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid (2.5 g, 10.33 mmol), 1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-amine (2.52 g, 12.4 mmol), EDCI (1.97 g, 10.33 mmol), HOBt (2.8 g, 20.6 mmol) and DIPEA (2.7 g, 20.66 mmol) in dry DMF (30 mL) was heated to 30° C. for 16 hours. Then water (30 mL) was added, the formed precipitate was separated by filtration and the filter cake was washed with water (10 mL) and dried to afford 1-(2-bromo-5H-pyrrolo[3,2-b]pyrazin-7-yl)-2-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-ylamino)ethanone (2.7 g, 61%) as a yellow solid. LCMS: (M+H)+=427.

Aufarbeitung

  1. customthe formed precipitate was separated by filtration
  2. washthe filter cake was washed with water (10 mL)
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d17f8b554c654555937882c3135fbfee
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

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