2-[6-(4-Benzyloxy-butyl)-benzoimidazol-1-yl]-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid ethyl ester → 4-(3-Chloro-phenyl)-2-[6-(4-hydroxy-butyl)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid ethyl ester

HRID 1667764Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1667764
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([N:11]2[C:15]3[CH:16]=[C:17]([CH2:20][CH2:21][CH2:22][CH2:23][O:24]CC4C=CC=CC=4)[CH:18]=[CH:19][C:14]=3[N:13]=[CH:12]2)=[N:8][C:7]=1[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[CH:33]=1)=[O:5])[CH3:2]>C(#N)C>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([N:11]2[C:15]3[CH:16]=[C:17]([CH2:20][CH2:21][CH2:22][CH2:23][OH:24])[CH:18]=[CH:19][C:14]=3[N:13]=[CH:12]2)=[N:8][C:7]=1[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[CH:33]=1)=[O:5])[CH3:2]

Komponenten

3

Edukt 1

HCID 674472132-[6-(4-Benzyloxy-butyl)-benzoimidazol-1-yl]-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid ethyl ester

Produkt 1

HCID 674467194-(3-Chloro-phenyl)-2-[6-(4-hydroxy-butyl)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid ethyl esterAusbeute 73,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a mixture of 0.434 g (0.795 mmole) of 2-[6-(4-benzyloxy-butyl)-benzoimidazol-1-yl]-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid ethyl ester (I.41c) and 5 mL of acetonitrile at 0 degrees was added dropwise 0.836 mL (0.795 mmole) of boron trifluoride-dimethyl sulfide complex. The mixture was stirred at ambient temperature for 2 hours and then concentrated under reduced pressure. Saturated sodium bicarbonate was added to the residue and the mixture was extracted three times with 15 mL of dichloromethane. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with methanol-dichloromethane (gradient 0:100-3:97) to give 0.266 g of 4-(3-chloro-phenyl)-2-[6-(4-hydroxy-butyl)-benzoimidazol-1-yl]-thiazole-5-carboxylic acid ethyl ester (I.41d) as a white solid.

Aufarbeitung

  1. additionwas added dropwise 0.836 mL (0.795 mmole) of boron trifluoride-dimethyl sulfide complex
  2. concentrationconcentrated under reduced pressure
  3. additionSaturated sodium bicarbonate was added to the residue
  4. extractionthe mixture was extracted three times with 15 mL of dichloromethane
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel chromatography
  10. washeluting with methanol-dichloromethane (gradient 0:100-3:97)

Quellen und Nachweise

ORD-Eintrag
ord-3c4989212cf741849fac1f83379db93a
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044213B2

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