Triethylamine → 1-(3-chloro-phenyl)-6-(4-nitro-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester

HRID 1241896Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1241896
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][N:9]=[C:10](Cl)[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[CH:6][CH:7]=1.N1([C:23]2[C:24](=[O:38])[N:25]([C:29]3[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=3)[CH2:26][CH2:27][CH:28]=2)CCOCC1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:14]([O:13][C:11]([C:10]1[C:28]2[CH2:27][CH2:26][N:25]([C:29]3[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=3)[C:24](=[O:38])[C:23]=2[N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[N:9]=1)=[O:12])[CH3:15]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 580329Acetic acid, chloro[(3-chlorophenyl)hydrazono]-, ethyl esterHCID 219368093-(4-Morpholinyl)-1-(4-nitrophenyl)-5,6-dihydro-2(1H)-pyridinone

Produkt 1

HCID 696667991-(3-chloro-phenyl)-6-(4-nitro-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl esterAusbeute 47,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Part A: A 500 mL flask was charged with N-(3-chlorophenyl)-1-(ethoxycarbonyl)-methanehydrazonoyl chloride (3.67 g, 14.1 mmol), 3-morpholin-4-yl-1-(4-nitro-phenyl)-5,6-dihydro-1H-pyridin-2-one (2.14 g, 7.05 mmol), 50 mL of toluene, and triethylamine (3.57 g, 35.3 mmol). The mixture was heated at 80° C. overnight. After cooling to room temperature, the reaction mixture was treated with trifuloroacetic acid (10.1 g) at rt for 5 h. The mixture was concentrated to dryness under reduced pressure. The residue was dissolved in methylene chloride, washed water and brine, and dried with sodium sulfate. The crude product, after evaporation of the solvent, was purified by silica gel chromatography, eluting with 1:2 ethyl acetate/hexane to yield 1-(3-chloro-phenyl)-6-(4-nitro-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester (1.48 g). 1H NMR (300 MHz, CDCl3) δ 8.24 (2H, d, J=9.1 Hz), 7.60 (1H, t, J=1.8 Hz), 7.52 (2H, d, J=9.1 Hz), 7.47˜7.36(2H, m), 4.48 (2H, q, J=7.0 Hz), 4.22 (2H, t, J=6.6 Hz), 3.39 (2H, t, J=6.6 Hz), 1.45 (3H, t, J=7.0 Hz) ppm.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. concentrationThe mixture was concentrated to dryness under reduced pressure
  3. dissolutionThe residue was dissolved in methylene chloride
  4. washwashed water and brine
  5. dry with materialdried with sodium sulfate
  6. customThe crude product, after evaporation of the solvent
  7. customwas purified by silica gel chromatography
  8. washeluting with 1:2 ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-8e53976f725f4bfaa82dd404107f1a9a
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115627B2

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