Trifluoroacetic acid → 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

HRID 914454Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 914454
C([O:5][C:6](=[O:39])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][N:18]([C:31]2[N:36]=[CH:35][C:34]([CH2:37][CH3:38])=[CH:33][N:32]=2)[CH2:19][C:20]2[CH:21]=[N:22][N:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:24]=2)[N:15]=1)([CH3:9])[CH3:8])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:37]([C:34]1[CH:33]=[N:32][C:31]([N:18]([CH2:19][C:20]2[CH:21]=[N:22][N:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:24]=2)[CH2:17][CH2:16][C:14]2[N:15]=[C:11]([S:10][C:7]([CH3:9])([CH3:8])[C:6]([OH:39])=[O:5])[S:12][CH:13]=2)=[N:36][CH:35]=1)[CH3:38]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 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 ester

Produkt 1

HCID 115625202-{[4-(2-{(5-ethylpyrimidin-2-yl)[(1-phenyl-1H-pyrazol-4-yl)methyl]amino}ethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acidAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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 (7.3 g) obtained in Example 326-1 was dissolved in dichloromethane (80 mL), trifluoroacetic acid (20 mL) was added, and the mixture was stirred at room temperature for 20 hr. The reaction mixture was concentrated under reduced pressure, ethyl acetate was added, and the mixture was washed with saturated aqueous sodium hydrogen carbonate solution (at this time point, the object product had been extracted in the ethyl acetate layer). The ethyl acetate layer was washed with aqueous 10% citric acid solution and 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=1:1 to 0:1) to give the title compound (5.0 g) as a white solid.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate
  2. additionwas added
  3. washthe mixture was washed with saturated aqueous sodium hydrogen carbonate solution (at this time point
  4. extractionthe object product had been extracted in the ethyl acetate layer)
  5. washThe ethyl acetate layer was washed with aqueous 10% citric acid solution and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=1:1 to 0:1)

Quellen und Nachweise

ORD-Eintrag
ord-b8119c8f9e1c4dca9a17751731f73ac7
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026370B2

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