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Hydrochloric Acid → 3-acetyl-4-amino-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-1,8-naphthyridin-2(1H)-one

HRID 13803
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 13803
[C:1]([C:4]1[C:5](=[O:34])[N:6]([CH3:33])[C:7]2[C:12]([C:13]=1[NH:14]C(=O)C)=[CH:11][C:10]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)=[C:9]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=1[Cl:32])[N:8]=2)(=[O:3])[CH3:2].Cl>O1CCOCC1.CCOC(C)=O>[C:1]([C:4]1[C:5](=[O:34])[N:6]([CH3:33])[C:7]2[C:12]([C:13]=1[NH2:14])=[CH:11][C:10]([C:18]1[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=1)=[C:9]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=1[Cl:32])[N:8]=2)(=[O:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 313Hydrochloric Acid2×HCID 11386747Naphthyridinone

Produkt 1

HCID 112600073-acetyl-4-amino-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-1,8-naphthyridin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To 16 mg of the product of Example 1 in 1,4-dioxane (1 mL) was added 0.5 mL of 1 M aqueous HCl solution. The reaction stirred at 50° C. for 5 hours. LC/MS indicated little product forming and an additional 0.2 mL of concentrated HCl solution was added. The temperature was increased to 90° C. for 4.5 hours at which point the reaction was cooled to room temperature and diluted with EtOAc. The solution was washed with saturated aqueous NaHCO3 solution before drying with Na2SO4 and concentrating. The residue was purified by preparative TLC (silica gel) eluted with 20% EtOAc in CH2Cl2 affording the title compound. HPLC/MS: 471.9 (M+1), 473.9 (M+3); Rt=4.32 min.

Aufarbeitung

  1. customforming
  2. temperatureThe temperature was increased to 90° C. for 4.5 hours at which
  3. temperaturewas cooled to room temperature
  4. washThe solution was washed with saturated aqueous NaHCO3 solution
  5. dry with materialbefore drying with Na2SO4
  6. concentrationconcentrating
  7. customThe residue was purified by preparative TLC (silica gel)
  8. washeluted with 20% EtOAc in CH2Cl2 affording the title compound

Quellen und Nachweise

ORD-Eintrag
ord-c547244f2ee541b2b0328425718be039
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07728141B2

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