Silicon tetrachloride → 3-(5-Chloro-pyridin-2-yl)-5-(5-isopropyl-tetrazol-1-yl)-benzoic acid methyl ester

HRID 84760

Reaktionsgleichung

Reaktionsgleichung von HRID 84760
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([NH:10][C:11](=O)[CH:12]([CH3:14])[CH3:13])[CH:7]=[C:6]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=2)[CH:5]=1.[N-:24]=[N+:25]=[N-:26].[Na+].[Si](Cl)(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>C(#N)C>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([N:10]2[C:11]([CH:12]([CH3:14])[CH3:13])=[N:26][N:25]=[N:24]2)[CH:7]=[C:6]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=2)[CH:5]=1

Komponenten

6

Edukt 4

HCID 24816Silicon tetrachlorideHCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 578514303-(5-Chloro-pyridin-2-yl)-5-isobutyrylamino-benzoic acid methyl ester

Produkt 1

HCID 578516043-(5-Chloro-pyridin-2-yl)-5-(5-isopropyl-tetrazol-1-yl)-benzoic acid methyl esterAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

3-(5-Chloro-pyridin-2-yl)-5-isobutyrylamino-benzoic acid methyl ester (1.90 g, 5.71 mmol) was dissolved in acetonitrile, and NaN3 (3.71 g, 5.71 mmol) and SiCl4 (1.64 mL, 14.28 mmol) were added. The reaction mixture was stirred at 60° C. for 18 hours, then cooled and poured in to cold saturated aqueous NaHCO3. The resulting mixture was extracted with EtOAc, and the combined organic layers were dried (MgSO4), filtered and concentrated under reduced pressure to give 1.84 g of 3-(5-chloro-pyridin-2-yl)-5-(5-isopropyl-tetrazol-1-yl)-benzoic acid methyl ester, MS (M+H)=358.

Aufarbeitung

  1. temperaturecooled
  2. extractionThe resulting mixture was extracted with EtOAc
  3. dry with materialthe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d200197e475f407bb45af5c3ae9065d5
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846945B2

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