Diisopropylethylamine → 5-Bromo-N3-[1-(6-quinolinyl)ethyl]-2,3-pyrazinediamine

HRID 16026

Reaktionsgleichung

Reaktionsgleichung von HRID 16026
[NH2:1][C:2]1[C:7](Br)=[N:6][C:5]([Br:9])=[CH:4][N:3]=1.[N:10]1[C:19]2[C:14](=[CH:15][C:16]([CH:20]([NH2:22])[CH3:21])=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1.CCN(C(C)C)C(C)C>CCCCO>[Br:9][C:5]1[N:6]=[C:7]([NH:22][CH:20]([C:16]2[CH:15]=[C:14]3[C:19](=[CH:18][CH:17]=2)[N:10]=[CH:11][CH:12]=[CH:13]3)[CH3:21])[C:2]([NH2:1])=[N:3][CH:4]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 6200042-Amino-3,5-dibromopyrazineHCID 208428591-(Quinolin-6-YL)ethanamine

Produkt 1

HCID 593417935-Bromo-N3-[1-(6-quinolinyl)ethyl]-2,3-pyrazinediamineAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-dibromopyrazine (5.1 g, 20 mmol) and 1-quinolin-6-yl-ethylamine (3.43 g, 20 mmol) in n-BuOH (5 mL) was added DIPEA (10.5 mL, 60 mmol). The reaction was irradiated in a microwave at 225° C. for 1 hour. The reaction mixture was concentrated and purified by column chromatography Biotage 40+M 0-50% EtOAc:Hexanes (7 column volume), 50-100% (10 column volume), and EtOAc with 10% MeOH to give 5-bromo-N*3*-(1-quinolin-6-yl-ethyl)-pyrazine-2,3-diamine (2.1 g, 66%).

Aufarbeitung

  1. customThe reaction was irradiated in a microwave at 225° C. for 1 hour
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by column chromatography Biotage 40+M 0-50% EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-61cc813be1b04660a84342b21efb7747
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732604B2

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