2-Hydrazinoquinoxaline → 3-Oxo-2-quinoxalin-2-yl-1,2,3,4,6,7-hexahydro-pyrazolo[4,3-c]pyridine-5-carboxylic acid tert-butyl ester

HRID 431648

Reaktionsgleichung

Reaktionsgleichung von HRID 431648
C(O[C:4]([CH:6]1[C:11](=O)[CH2:10][CH2:9][N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7]1)=[O:5])C.[N:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=[CH:22][C:21]=1[NH:30][NH2:31]>C1(C)C=CC=CC=1>[C:16]([O:15][C:13]([N:8]1[CH2:9][CH2:10][C:11]2[NH:31][N:30]([C:21]3[CH:22]=[N:23][C:24]4[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=4)[N:20]=3)[C:4](=[O:5])[C:6]=2[CH2:7]1)=[O:14])([CH3:17])([CH3:18])[CH3:19]

Komponenten

4

Edukt 2

HCID 2898472-HydrazinoquinoxalineHCID 64208761-(1,1-Dimethylethyl) 3-ethyl 4-oxo-1,3-piperidinedicarboxylate

Produkt 1

HCID 697341853-Oxo-2-quinoxalin-2-yl-1,2,3,4,6,7-hexahydro-pyrazolo[4,3-c]pyridine-5-carboxylic acid tert-butyl esterAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 4-oxo-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (500 mg, 1.84 mmol; Tetrahedron 1994, 50, 515) in toluene (10 mL) was added quinoxalin-2-yl-hydrazine (295 mg, 1.85 mmol; Heterocycles 1985, 23, 2603). This mixture was stirred at reflux overnight, cooled to room temperature, concentrated, and purified by flash column chromatography (25→75% ethyl acetate/hexanes) to give 600 mg (89%) of the title compound of Example 75, Step A as a light orange solid. 1H NMR (CDCl3, 250 MHz, 5:1 mixture of tautomers) δ 11.94 (br s, 0.83H), 10.16 (s, 0.17H), 9.57 (s, 0.83H), 8.13 (dd, 1H), 7.91-7.69 (c, 3H), 4.45 (s, 1.66H), 4.33 (s, 0.34H), 3.79-3.72 (c, 2H), 2.82-2.72 c, 2H), 1.52 (s, 9H); MS (APCI) 368 (MH+).

Aufarbeitung

  1. temperatureat reflux overnight
  2. concentrationconcentrated
  3. custompurified by flash column chromatography (25→75% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-ca9e2b88d06840c5ad166ca11ca9792a
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06660740B1

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