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

HRID 1667763Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1667763
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([N:11]2[C:15]3[CH:16]=[C:17]([CH:20]=[CH:21][CH2:22][CH2:23][O:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=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].O1CCCC1>[Pd].C(O)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][O:24][CH2:25][C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=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]

Komponenten

5

Edukt 2

HCID 8028TetrahydrofuranHCID 674446332-[6-(-Benzyloxy-but-1-enyl)-benzoimidazol-1-yl]-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid ethyl ester

Produkt 1

HCID 674472132-[6-(4-Benzyloxy-butyl)-benzoimidazol-1-yl]-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid ethyl esterAusbeute 76,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 0.568 g of 2-[6-(-benzyloxy-but-1-enyl)-benzoimidazol-1-yl]-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid ethyl ester (I.41b), 5 mL of tetrahydrofuran, 5 mL of ethanol, and 0.30 g of 10% palladium on carbon catalyst was hydrogenated at 50 psi overnight. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with methanol-dichloromethane (gradient 0:100-2:98) to give 0.434 g of 2-[6-(4-benzyloxy-butyl)-benzoimidazol-1-yl]-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid ethyl ester (I.41c) as white solid.

Aufarbeitung

  1. customwas hydrogenated at 50 psi overnight
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with methanol-dichloromethane (gradient 0:100-2:98)

Quellen und Nachweise

ORD-Eintrag
ord-8038fdbaed3a463ab29710af19742d33
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044213B2

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