Potassium Carbonate → 5-Methyl-1-((S)-1-phenylethyl)-6-(quinolin-5-YL)-1H-imidazo[4,5-B]pyrazin-2(3H)-one

HRID 388098

Reaktionsgleichung

Reaktionsgleichung von HRID 388098
[CH3:1][C:2]1[N:3]=[C:4]([NH2:27])[C:5]([NH:18][C@H:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH3:20])=[N:6][C:7]=1[C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[N:13]2.BrC1N=C(N[C@H](C2C=CC=CC=2)C)C(N)=NC=1C.N1C2C=CC=C(B(O)O)C=2C=CC=1.[C:59](=O)([O-])[O-:60].[K+].[K+]>O.CN(C)C=O.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>[CH3:1][C:2]1[N:3]=[C:4]2[NH:27][C:59](=[O:60])[N:18]([C@H:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH3:20])[C:5]2=[N:6][C:7]=1[C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[N:13]2

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 5153389Quinolin-5-ylboronic acidHCID 688536935-Methyl-N2-((S)-1-phenylethyl)-6-(quinolin-5-yl)pyrazine-2,3-diamineHCID 86626389(S)-6-bromo-5-methyl-N2-(1-phenylethyl)pyrazine-2,3-diamine

Produkt 1

HCID 249850255-Methyl-1-((S)-1-phenylethyl)-6-(quinolin-5-YL)-1H-imidazo[4,5-B]pyrazin-2(3H)-oneAusbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-Methyl-N2-((S)-1-phenylethyl)-6-(quinolin-5-yl)pyrazine-2,3-diamine. A solution of (S)-6-bromo-5-methyl-N2-(1-phenylethyl)pyrazine-2,3-diamine (0.975 g, 3.19 mmol), quinoline-5-boronic acid (0.606 g, 3.50 mmol), tetrakis(triphenylphosphine)palladium (0.368 g, 0.319 mmol), and potassium carbonate (1.76 g, 12.76 mmol) in water (8 mL) and dimethylformamide (30 mL) was reacted according to General Procedure B and purified via Biotage silica gel chromatography (0-10% methanol in dichloromethane, 40M column). The resultant solid was triturated with water/methanol to afford the title compound (0.200 g, 18% yield). MS (ESI) m/z 356.5 [M+1]+.

Aufarbeitung

  1. custompurified via Biotage silica gel chromatography (0-10% methanol in dichloromethane, 40M column)
  2. customThe resultant solid was triturated with water/methanol

Quellen und Nachweise

ORD-Eintrag
ord-51bc88db9e3e4e33a1ae6d8260220258
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372976B2

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