Water → 2-{[4-(2-{(5-ethylpyrimidin-2-yl)[(1-phenyl-1H-pyrazol-4-yl)methyl]amino}ethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester

HRID 914453Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 914453
[C:1]([O:5][C:6](=[O:27])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][NH:18][C:19]2[N:24]=[CH:23][C:22]([CH2:25][CH3:26])=[CH:21][N:20]=2)[N:15]=1)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].Cl[CH2:29][C:30]1[CH:31]=[N:32][N:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:34]=1.CC(C)([O-])C.[K+].O>CN(C)C=O>[C:1]([O:5][C:6](=[O:27])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][N:18]([C:19]2[N:20]=[CH:21][C:22]([CH2:25][CH3:26])=[CH:23][N:24]=2)[CH2:29][C:30]2[CH:31]=[N:32][N:33]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH:34]=2)[N:15]=1)([CH3:9])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Komponenten

6

Edukt 4

HCID 962WaterHCID 21211624-(chloromethyl)-1-phenyl-1H-pyrazoleHCID 23665647Potassium tert-butoxideHCID 597588712-[(4-{2-[(5-Ethylpyrimidin-2-yl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester

Produkt 1

HCID 597589302-{[4-(2-{(5-ethylpyrimidin-2-yl)[(1-phenyl-1H-pyrazol-4-yl)methyl]amino}ethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl esterAusbeute 75,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-[(4-{2-[(5-Ethylpyrimidin-2-yl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester (7.0 g) synthesized in Example 265-1 and 4-(chloromethyl)-1-phenyl-1H-pyrazole (3.47 g) synthesized in Reference Example 18 were dissolved in N,N-dimethylformamide (80 mL), potassium tert-butoxide (2.32 g) was added thereto, and the mixture was stirred at room temperature for 8 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=4:1 to 3:1) to give the title compound (7.30 g) as a colorless oil.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=4:1 to 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-f162f6c63b2f4fa58b14819f6a5f4e12
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026370B2

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