Ethyl 4-(furan-2-yl)-2,4-dioxobutanoate → 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-furan-2-yl-1H-pyrazole-3-carboxylic acid ethyl ester

HRID 33248Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 33248
[CH2:1]([O:3][C:4](=[O:15])[C:5](=O)[CH2:6][C:7]([C:9]1[O:10][CH:11]=[CH:12][CH:13]=1)=O)[CH3:2].[Cl:16][C:17]1[S:21][C:20]([C:22]2[O:26][N:25]=[C:24]([CH2:27][NH:28][NH2:29])[CH:23]=2)=[CH:19][CH:18]=1>C(O)(=O)C.O>[CH2:1]([O:3][C:4]([C:5]1[CH:6]=[C:7]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)[N:28]([CH2:27][C:24]2[CH:23]=[C:22]([C:20]3[S:21][C:17]([Cl:16])=[CH:18][CH:19]=3)[O:26][N:25]=2)[N:29]=1)=[O:15])[CH3:2]

Komponenten

5

Edukt 2

HCID 3006753Ethyl 4-(furan-2-yl)-2,4-dioxobutanoateHCID 23033477[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-hydrazine

Produkt 1

HCID 602079551-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-furan-2-yl-1H-pyrazole-3-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 550 mg 4-Furan-2-yl-2,4-dioxo-butyric acid ethyl ester and 601 mg [5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-hydrazine in 10 ml acetic acid was heated to 80° C. for 2 h. Then the reaction mixture was diluted with 20 ml water and extracted with ethyl acetate (3×100 ml). The combined organic layers were dried over MgSO4. The solvents were removed under reduced pressure and the residue was purified by silica gel chromatography eluting with a n-heptane:ethyl acetate gradient 100%->50%.

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×100 ml)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. customThe solvents were removed under reduced pressure
  4. customthe residue was purified by silica gel chromatography
  5. washeluting with a n-heptane

Quellen und Nachweise

ORD-Eintrag
ord-e41909bb60644df8b2ad6cf8d249f3f5
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429581B2

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