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

HRID 256905Notes

Reaction equation

HRID 256905 reaction equation
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]

Participants

7

Reactant 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

Product 1

HCID 217086395-(3-Hexylthio-1,2,5-thiadiazol-4-yl)-1-azabicyclo[3.2.1]octane oxalateYield 49.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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-bromohexan (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.

Workup

  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

Sources & evidence

ORD record
ord-d53536103116448e8dcae9823fbf6f66
Source dataset
uspto-grants-1993_11
Patent number
US05260314

Reaction notes

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