1-Bromohexane → 5-(3-Hexylthio-1,2,5-thiadiazol-4-yl)-1-azabicyclo[3.2.1]octane oxalate

HRID 649795Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 649795
O.[SH-:2].[Na+].[C:4]([OH:9])(=[O:8])[C:5]([OH:7])=[O:6].Cl[C:11]1[C:15]([C:16]23[CH2:23][N:20]([CH2:21][CH2:22]2)[CH2:19][CH2:18][CH2:17]3)=[N:14][S:13][N:12]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>CN(C=O)C.O>[C:4]([OH:9])(=[O:8])[C:5]([OH:7])=[O:6].[CH2:31]([S:2][C:11]1[C:15]([C:16]23[CH2:23][N:20]([CH2:21][CH2:22]2)[CH2:19][CH2:18][CH2:17]3)=[N:14][S:13][N:12]=1)[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Komponenten

7

Edukt 4

HCID 81011-BromohexaneHCID 11430Potassium CarbonateHCID 16211346Sodium hydrosulfide hydrateHCID 217086095-(3-Chloro-1,2,5-thiadiazol-4-yl)-1-azabicyclo[3.2.1]octane oxalate

Produkt 1

HCID 217086395-(3-Hexylthio-1,2,5-thiadiazol-4-yl)-1-azabicyclo[3.2.1]octane oxalateAusbeute 49,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium hydrosulfide monohydrate (326 mg, 4.4 mmol) was added to a solution of 5-(3-chloro-1,2,5-thiadiazol-4-yl)-1-azabicyclo[3.2.1]octane oxalate (350 mg, 1.1 mmol) in DMF (20 ml) at room temperature and the reaction mixture was stirred for 30 min. Potassium carbonate (1.24 g, 9 mmol) and 1-bromohexane (561 μl, 4 mmol) were added and the reaction mixture was stirred for 3 h. Water (50 ml) was added to the reaction mixture and the aqueous phase extracted with ether (3×200 ml). The combined ether phases were dried and evaporated to give the crude free base of the title compound (220 mg). The residue was crystallized as the oxalate salt from acetone to give the title compound. Yield 200 mg (Compound 68), M.p. 67-69° C.

Aufarbeitung

  1. stirringthe reaction mixture was stirred for 3 h
  2. extractionthe aqueous phase extracted with ether (3×200 ml)
  3. dry with materialThe combined ether phases were dried
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-461a08288dc342c396149de432d85b55
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06271229B1

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