Ammonia → 1-(4-Fluorobenzyl)-5-methanesulfonylindole-2-carboxamide

HRID 1814099

Reaktionsgleichung

Reaktionsgleichung von HRID 1814099
[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:20](O)=[O:21])=[CH:4][CH:3]=1.O1CCCC1.C(Cl)(=O)OCC.[NH3:36]>O.C(N(CC)CC)C>[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:20]([NH2:36])=[O:21])=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 10928Ethyl chloroformateHCID 225044521-(4-fluorobenzyl)-5-methanesulfonylindole-2-carboxylic Acid

Produkt 1

HCID 225043691-(4-Fluorobenzyl)-5-methanesulfonylindole-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a mixture of the compound obtained in Example 22 (4) (0.23 g) and tetrahydrofuran (7 ml), triethylamine (0.19 ml) and ethyl chlorocarbonate (0.1 ml) were added at 0° C. and the mixture was stirred at the same temperature for 20 minutes. An ammonia gas was blown into the mixture at 0° C. and the mixture was stirred at the same temperature for 30 minutes. Water was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was recrystallized (ethyl acetate) to obtain 0.06 g of the desired product as a white crystal.

Aufarbeitung

  1. additionwere added at 0° C.
  2. customwas blown into the mixture at 0° C.
  3. stirringthe mixture was stirred at the same temperature for 30 minutes
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was recrystallized (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-078af033a05e40ef886904d72cdff349
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06875770B2

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