Ethyl Acetate → N,N-Dicyclopropylmethyl-N-[7-[2-methoxy-6-methyl-4-(1,3-thiazol-2-yl)phenyl]-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]amine

HRID 9218

Reaktionsgleichung

Reaktionsgleichung von HRID 9218
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[N:14]3[N:15]=[C:16]([S:27][CH3:28])[C:17]([N:18]([CH2:23][CH:24]4[CH2:26][CH2:25]4)[CH2:19][CH:20]4[CH2:22][CH2:21]4)=[C:13]3[CH:12]=[CH:11][CH:10]=2)=[C:4]([O:29][CH3:30])[CH:3]=1.C([Sn]([C:44]1[S:45][CH:46]=[CH:47][N:48]=1)(CCCC)CCCC)CCC.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH:20]1([CH2:19][N:18]([CH2:23][CH:24]2[CH2:26][CH2:25]2)[C:17]2[C:16]([S:27][CH3:28])=[N:15][N:14]3[C:9]([C:5]4[C:6]([CH3:8])=[CH:7][C:2]([C:44]5[S:45][CH:46]=[CH:47][N:48]=5)=[CH:3][C:4]=4[O:29][CH3:30])=[CH:10][CH:11]=[CH:12][C:13]=23)[CH2:22][CH2:21]1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 21984504N-[7-(4-bromo-2-methoxy-6-methylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]-N,N-dicyclopropylmethylamine

Produkt 1

HCID 21984786N,N-Dicyclopropylmethyl-N-[7-[2-methoxy-6-methyl-4-(1,3-thiazol-2-yl)phenyl]-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]amineAusbeute 66,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

After dissolving N-[7-(4-bromo-2-methoxy-6-methylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]-N,N-dicyclopropylmethylamine (45 mg) in toluene (0.60 mL), tributylstannylthiazole (52 mg) and tetrakis (triphenylphosphine)palladium (0) complex (9 mg) were added, the mixture was heated and stirred at 120° C. for 2 hours and then cooled to room temperature, and ethyl acetate was added. After filtering out the precipitated insoluble portion, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:5) to obtain the title compound (30 mg) as white crystals.

Aufarbeitung

  1. additionwere added
  2. temperaturethe mixture was heated
  3. temperaturecooled to room temperature
  4. filtrationAfter filtering out the precipitated insoluble portion
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:5)

Quellen und Nachweise

ORD-Eintrag
ord-1d28720315fc4f67a65cac0df851c4fc
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091215B2

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