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Formic Acid → 3-{3-[N-(2-(3,4-Dimethoxyphenyl)-ethyl)-N-methylamino]-propyloxy}-5-(3,4-dimethoxyphenyl)-pyrazole

HRID 1489655
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1489655
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]([CH2:15][CH2:16][CH2:17][O:18][C:19]2[N:20](CC3C=CC=CC=3)[N:21]=[C:22]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=3)[CH:23]=2)[CH3:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(O)=O>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]([CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=3)[NH:21][N:20]=2)[CH3:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 284Formic AcidHCID 229023713-{3-[N-(2-(3,4-Dimethoxyphenyl)-ethyl)-N-methylamino]-propyloxy}-5-(3,4-dimethoxyphenyl)-2-benzyl-pyrazole

Produkt 1

HCID 152835203-{3-[N-(2-(3,4-Dimethoxyphenyl)-ethyl)-N-methylamino]-propyloxy}-5-(3,4-dimethoxyphenyl)-pyrazoleAusbeute 95,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysator
HCID 887
Methanol
Lösungsmittel

Versuchsvorschrift

2 g of 3-{3-[N-(2-(3,4-Dimethoxyphenyl)-ethyl)-N-methylamino]-propyloxy}-5-(3,4-dimethoxyphenyl)-2-benzyl-pyrazole prepared according to Example 13 were dissolved in 10 ml of methanol and added to 2 g of palladium black under nitrogen. 5.5 ml of 98% strength formic acid were added to the solution, which was stirred under nitrogen. After the mixture had been stirred for 3 hours under nitrogen the catalyst was filtered out, and the filtrate was concentrated by evaporation. The oily residue was taken up in saturated sodium carbonate solution and extracted repeatedly with ethyl acetate. The combined organic phases were dried with sodium sulfate and concentrated by evaporation. 1.6 g of 3-{3-[N-(2-(3,4-Dimethoxyphenyl)-ethyl)-N-methylamino]-propyloxy}-5-(3,4-dimethoxyphenyl)-pyrazole were obtained as an oily base. This base was converted analogously to Example 1E) into the hydrochloride having a melting point of 189° to 192° C.

Aufarbeitung

  1. stirringAfter the mixture had been stirred for 3 hours under nitrogen the catalyst
  2. filtrationwas filtered out
  3. concentrationthe filtrate was concentrated by evaporation
  4. extractionextracted repeatedly with ethyl acetate
  5. dry with materialThe combined organic phases were dried with sodium sulfate
  6. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-2d2ed27c97724bc98b184a7f98bd770b
Quelldatensatz
uspto-grants-1997_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05679699

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