Water → 2-Methyl-2-({4-[2-(methyl{5-[4-(trifluoromethoxy)phenyl]pyrimidin-2-yl}amino)ethyl]-1,3-thiazol-2-yl}thio)propionic acid tert-butyl ester

HRID 914348Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 914348
[C:1]([O:5][C:6](=[O:36])[C:7]([CH3:35])([S:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][CH2:16][NH:17][C:18]2[N:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([O:30][C:31]([F:34])([F:33])[F:32])=[CH:26][CH:25]=3)=[CH:20][N:19]=2)[N:14]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].CI.[CH3:39]C(C)([O-])C.[K+].O>CN(C)C=O>[C:1]([O:5][C:6](=[O:36])[C:7]([CH3:8])([S:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][CH2:16][N:17]([CH3:39])[C:18]2[N:19]=[CH:20][C:21]([C:24]3[CH:25]=[CH:26][C:27]([O:30][C:31]([F:32])([F:34])[F:33])=[CH:28][CH:29]=3)=[CH:22][N:23]=2)[N:14]=1)[CH3:35])([CH3:2])([CH3:3])[CH3:4]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 597590702-Methyl-2-({4-[2-({5-[4-(trifluoromethoxy)phenyl]pyrimidin-2-yl}amino)ethyl]-1,3-thiazol-2-yl}thio)propionic acid tert-butyl ester

Produkt 1

HCID 597593932-Methyl-2-({4-[2-(methyl{5-[4-(trifluoromethoxy)phenyl]pyrimidin-2-yl}amino)ethyl]-1,3-thiazol-2-yl}thio)propionic acid tert-butyl esterAusbeute 33,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-Methyl-2-({4-[2-({5-[4-(trifluoromethoxy)phenyl]pyrimidin-2-yl}amino)ethyl]-1,3-thiazol-2-yl}thio)propionic acid tert-butyl ester (620 mg) synthesized in Example 162-2 and methyl iodide (325 mg) were dissolved in N,N-dimethylformamide (6.0 mL), potassium tertiary butoxide (154 mg) was added, 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=3:1) to give the title compound (215 mg) 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=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-0c6ab5bc5036413c9a8f6f49f7ec75c6
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026370B2

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