Methyl pyruvate → 8-(2,4-dichloro-phenyl)-4-(2-methoxy-1-methyl-ethyl)-2-methyl-4H-pyrido[2,3-b]pyrazin-3-one

HRID 1831509Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1831509
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][N:12]=[C:11]([NH:15][CH:16]([CH3:20])[CH2:17][O:18][CH3:19])[C:10]=1[NH2:21].[C:22](OC)(=[O:26])[C:23]([CH3:25])=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]2[N:21]=[C:23]([CH3:25])[C:22](=[O:26])[N:15]([CH:16]([CH3:20])[CH2:17][O:18][CH3:19])[C:11]=2[N:12]=[CH:13][CH:14]=1

Komponenten

4

Edukt 2

HCID 11748Methyl pyruvateHCID 627056514-(2,4-dichloro-phenyl)-N2-(2-methoxy-1-methyl-ethyl)-pyridine-2,3-diamine

Produkt 1

HCID 220520698-(2,4-dichloro-phenyl)-4-(2-methoxy-1-methyl-ethyl)-2-methyl-4H-pyrido[2,3-b]pyrazin-3-oneAusbeute 2,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

4-(2,4-Dichloro-phenyl)-N2-(2-methoxy-1-methyl-ethyl)-pyridine-2,3-diamine (0.13 g, 0.40 mmol) was dissolved in toluene (20 mL), followed by methyl pyruvate (0.081 g, 0.80 mmol) and heated at reflux overnight. The reaction was concentrated in vacuo and purified by reverse phase prep HPLC to yield 3.2 mg (2%) of 8-(2,4-dichloro-phenyl)-4-(2-methoxy-1-methyl-ethyl)-2-methyl-4H-pyrido[2,3-b]pyrazin-3-one (Example 9): 1H NMR (300 MHz, CD3OD): δ 8.6 (d, 1H), 7.6 (s, 1H), 7.4–7.25 (m, 3H), 4.4 (m, 1H). 3.8 (m, 1H), 3.3 (s, 3H), 2.4 (s, 3H), 1.6 (d, 2H), 1.25 (s, 2H). MS (AP) m/z 378.3 [(M+H)+, 100].

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux overnight
  3. concentrationThe reaction was concentrated in vacuo
  4. custompurified by reverse phase prep HPLC

Quellen und Nachweise

ORD-Eintrag
ord-d8d355299af64dc99a40f3ebc1038783
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07067658B2

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