Water → 1-{4-[5-(2-Fluorobiphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]benzyl}-4-(pyridin-2-ylcarbamoyl)piperidine-4-carboxylic acid benzyl ester

HRID 2407514Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2407514
C(N(CC)CC)C.[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.[CH2:15]([O:22][C:23]([C:25]1([C:56](Cl)=[O:57])[CH2:30][CH2:29][N:28]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]3[N:42]=[C:41]([C:43]4[CH:48]=[CH:47][C:46]([C:49]5[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=5)=[C:45]([F:55])[CH:44]=4)[O:40][N:39]=3)=[CH:34][CH:33]=2)[CH2:27][CH2:26]1)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>ClCCl>[CH2:15]([O:22][C:23]([C:25]1([C:56](=[O:57])[NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH2:26][CH2:27][N:28]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]3[N:42]=[C:41]([C:43]4[CH:48]=[CH:47][C:46]([C:49]5[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=5)=[C:45]([F:55])[CH:44]=4)[O:40][N:39]=3)=[CH:34][CH:33]=2)[CH2:29][CH2:30]1)=[O:24])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 104392-AminopyridineHCID 866461104-Chlorocarbonyl-1-{4-[5-(2-fluorobiphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]benzyl}-piperidine-4-carboxylic acid benzyl ester

Produkt 1

HCID 595094831-{4-[5-(2-Fluorobiphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]benzyl}-4-(pyridin-2-ylcarbamoyl)piperidine-4-carboxylic acid benzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred solution of triethyl amine (0.34 g, 0.0034 mol) in dichloromethane (20 mL), 2-amino pyridine (0.152 g, 0.0016 mol) is added. A solution of 4-chlorocarbonyl-1-{4-[5-(2-fluorobiphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]benzyl}-piperidine-4-carboxylic acid benzyl ester in dichloromethane (10 mL) is added slowly into the reaction mixture at 0-50 C. It is then stirred at room temperature for 1 hr. Demineralized water (15 mL) is added to the reaction mixture, organic layer is separated and the aqueous layer is extracted with (1×20 mL) dichloromethane. Combined organic layer is dried over sodium sulphate and concentrated under reduced pressure to get the crude material, which is purified by column chromatography (silica gel 230-400 mesh, n-hexane:ethyl acetate 60:40) to furnish 1-{4-[5-(2-fluorobiphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]benzyl}-4-(pyridin-2-ylcarbamoyl)piperidine-4-carboxylic acid benzyl ester (138) (BS6.555).

Aufarbeitung

  1. customis separated
  2. extractionthe aqueous layer is extracted with (1×20 mL) dichloromethane
  3. dry with materialCombined organic layer is dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customto get the crude material, which
  6. customis purified by column chromatography (silica gel 230-400 mesh, n-hexane:ethyl acetate 60:40)

Quellen und Nachweise

ORD-Eintrag
ord-215867d475f642ea8300dd83c9d51665
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08809539B2

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