Hydrochloric Acid → 3-(3-Pentylthio-1,2,5-thiadiazol-4-yl)-1-azabicyclo[2.2.2]octane fumarate

HRID 649790Notes

Reaction equation

HRID 649790 reaction equation
[C:1](O)(=O)[C:2]([OH:4])=[O:3].Cl[C:8]1[C:12]([CH:13]2[CH:18]3[CH2:19][CH2:20][N:15]([CH2:16][CH2:17]3)[CH2:14]2)=[N:11][S:10][N:9]=1.O.[SH2:22].[Na].[C:24](=[O:27])([O-])[O-:25].[K+].[K+].[CH2:30](Br)[CH2:31][CH2:32][CH2:33][CH3:34].Cl>CN(C=O)C>[C:24]([OH:25])(=[O:27])/[CH:8]=[CH:1]/[C:2]([OH:4])=[O:3].[CH2:30]([S:22][C:8]1[C:12]([CH:13]2[CH:18]3[CH2:19][CH2:20][N:15]([CH2:16][CH2:17]3)[CH2:14]2)=[N:11][S:10][N:9]=1)[CH2:31][CH2:32][CH2:33][CH3:34]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 80571-BromopentaneHCID 11430Potassium CarbonateHCID 217085453-(3-Chloro-1,2,5-thiadiazol-4-yl)-1-azabicyclo[2.2.2]octane oxalateHCID 53442613Sodium hydrogen sulfide hydrate

Product 1

HCID 217085713-(3-Pentylthio-1,2,5-thiadiazol-4-yl)-1-azabicyclo[2.2.2]octane fumarate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(3-chloro-1,2,5-thiadiazol-4-yl)-1-azabicyclo[2.2.2]octane oxalate (500 mg, 1.56 mmol), sodiumhydrogen sulfide, monohydrate (463 mg, 6.25 mmol) and potassium carbonate (1.38 g, 10 mmol) in DMF (20 ml) was stirred at room temperature for 1 h. 1-Pentylbromide (755 mg, 5 mmol) was added, and the reaction mixture was stirred at room temperature for 18 h. 1N HCl was added, and the mixture extracted with ether once. 50% NaOH was added to the aqueous phase and extracted with ether. The ether phase was dried and evaporated. Crystallization of the residue with fumaric acid from isopropanol/ether gave the title compound in 380 mg yield. (Compound 12). M.p. 138-139° C.

Workup

  1. extractionthe mixture extracted with ether once
  2. addition50% NaOH was added to the aqueous phase
  3. extractionextracted with ether
  4. dry with materialThe ether phase was dried
  5. customevaporated
  6. customCrystallization of the residue with fumaric acid from isopropanol/ether

Sources & evidence

ORD record
ord-05430331c28b4677b4bc52bd767328bf
Source dataset
uspto-grants-2001_08
Patent number
US06271229B1

Reaction notes

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