Potassium Carbonate → (R)-1-(1-PHENYLPROPYL)-6-(QUINOLIN-5-YL)-1H-IMIDAZO[4,5-b]PYRAZIN-2(3H)-ONE

HRID 388093

Reaktionsgleichung

Reaktionsgleichung von HRID 388093
[C:1]1([C@H:7]([NH:10][C:11]2[C:16]([NH2:17])=[N:15][CH:14]=[C:13]([C:18]3[CH:27]=[CH:26][CH:25]=[C:24]4[C:19]=3[CH:20]=[CH:21][CH:22]=[N:23]4)[N:12]=2)[CH2:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.BrC1N=C(N[C@@H](C2C=CC=CC=2)CC)C(N)=NC=1.N1C2C=CC=C(B(O)O)C=2C=CC=1.[C:59](=O)([O-])[O-:60].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C)C=O.O>[C:1]1([C@H:7]([N:10]2[C:11]3=[N:12][C:13]([C:18]4[CH:27]=[CH:26][CH:25]=[C:24]5[C:19]=4[CH:20]=[CH:21][CH:22]=[N:23]5)=[CH:14][N:15]=[C:16]3[NH:17][C:59]2=[O:60])[CH2:8][CH3:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 5153389Quinolin-5-ylboronic acidHCID 68853964(R)-N2-(1-phenylpropyl)-6-(quinolin-5-yl)pyrazine-2,3-diamineHCID 86626386(R)-6-Bromo-N2-(1-phenylpropyl)pyrazine-2,3-diamine

Produkt 1

HCID 66699594(R)-1-(1-PHENYLPROPYL)-6-(QUINOLIN-5-YL)-1H-IMIDAZO[4,5-b]PYRAZIN-2(3H)-ONEAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(R)-N2-(1-phenylpropyl)-6-(quinolin-5-yl)pyrazine-2,3-diamine. (R)-6-Bromo-N2-(1-phenylpropyl)pyrazine-2,3-diamine (0.440 g, 1.43 mmol), quinoline-5-boronic acid (0.273 g, 1.58 mmol), tetrakis(triphenylphosphine)palladium (0.165 g, 0.143 mmol), potassium carbonate (0.789 g, 5.72 mmol), water (8 mL) and dimethylformamide (30 mL) were reacted according to General Procedure B. The crude was purified via Biotage silica gel chromatography (0-10% methanol/dichloromethane, 40S column) to afford the title compound (0.476 g, 93% yield). MS (ESI) m/z 356.4 [M+1]+.

Aufarbeitung

  1. customThe crude was purified via Biotage silica gel chromatography (0-10% methanol/dichloromethane, 40S column)

Quellen und Nachweise

ORD-Eintrag
ord-8a0acac74f0f457897a5d23e595e3049
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372976B2

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