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Tert-butyl({5-[5-chloro-3-fluoro-2-(2-methyl-2h-tetrazol-5-yl)phenyl]-3-fluoropyridin-2-yl}methyl)carbamate → ({5-[5-Chloro-3-fluoro-2-(2-methyl-2h-tetrazol-5-yl)phenyl]-3-fluoropyridin-2-yl}methyl)amine

HRID 1160605
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1160605
C(OC(=O)[NH:7][CH2:8][C:9]1[C:14]([F:15])=[CH:13][C:12]([C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([F:23])[C:17]=2[C:24]2[N:25]=[N:26][N:27]([CH3:29])[N:28]=2)=[CH:11][N:10]=1)(C)(C)C>CCOC(C)=O>[Cl:22][C:20]1[CH:19]=[C:18]([F:23])[C:17]([C:24]2[N:25]=[N:26][N:27]([CH3:29])[N:28]=2)=[C:16]([C:12]2[CH:13]=[C:14]([F:15])[C:9]([CH2:8][NH2:7])=[N:10][CH:11]=2)[CH:21]=1
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Komponenten

3

Edukt 1

HCID 68451751Tert-butyl({5-[5-chloro-3-fluoro-2-(2-methyl-2h-tetrazol-5-yl)phenyl]-3-fluoropyridin-2-yl}methyl)carbamate

Produkt 1

HCID 68452622({5-[5-Chloro-3-fluoro-2-(2-methyl-2h-tetrazol-5-yl)phenyl]-3-fluoropyridin-2-yl}methyl)amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The above carbamate was dissolved in 50 mL of dry EtOAc. Anhydrous HCl gas was then bubbled through the solution for 3 minutes. The reaction was stirred vigorously for one hour. The reaction mixture was slowly neutralized with a saturated aqueous sodium bicarbonate solution. The mixture was partitioned between water and EtOAc. The organic layer was washed with water and brine prior to drying over sodium sulfate. The extracts were filtered, concentrated, and purified by chromatography on silica gel eluting with 0-20% MeOH in dichloromethane to provide ({5-[5-chloro-3-fluoro-2-(2-methyl-2H-tetrazol-5-yl)phenyl]-3-fluoropyridin-2-yl}methyl)amine.

Aufarbeitung

  1. customAnhydrous HCl gas was then bubbled through the solution for 3 minutes
  2. customThe mixture was partitioned between water and EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialto drying over sodium sulfate
  5. filtrationThe extracts were filtered
  6. concentrationconcentrated
  7. custompurified by chromatography on silica gel eluting with 0-20% MeOH in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-8e5198affd544743acdae1d9e73d438b
Quelldatensatz
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07816380B2

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