4-Bromo-2-thiophenecarboxylic Acid → HCID 23599474, compound

HRID 1726339Notes

Reaction equation

HRID 1726339 reaction equation
Cl.Cl.[N:3]12[CH2:10][CH2:9][CH:6]([CH2:7][CH2:8]1)[C@@H:5]([NH2:11])[CH2:4]2.[Br:12][C:13]1[CH:14]=[C:15]([C:18](O)=[O:19])[S:16][CH:17]=1>>[N:3]12[CH2:10][CH2:9][CH:6]([CH2:7][CH2:8]1)[C@@H:5]([NH:11][C:18]([C:15]1[S:16][CH:17]=[C:13]([Br:12])[CH:14]=1)=[O:19])[CH2:4]2

Participants

3

Reactant 2

HCID 6104094-Bromo-2-thiophenecarboxylic AcidHCID 12494972(R)-(+)-3-Aminoquinuclidine Dihydrochloride

Product 1

HCID 23599474HCID 23599474, compound

Procedure

Prepared by a method analogous to that described for the preparation of Intermediate 1 from (R)-1-azabicyclo[2.2.2]oct-3-ylamine dihydrochloride and 4-bromothiophene-2-carboxylic acid. The residue from evaporation of the reaction mixture was partitioned between aqueous hydrochloric acid and chloroform. The aqueous layer was then basified with aqueous sodium hydroxide and extracted with chloroform. The organic extracts were dried (MgSO4), filtered, and evaporated and resulting solid was recrystallised from ethyl acetate/hexane to give the title compound as a colourless solid; MS (ES+) 315, 317 (MH+).

Workup

  1. customPrepared by a method analogous to
  2. customThe residue from evaporation of the reaction mixture
  3. customwas partitioned between aqueous hydrochloric acid and chloroform
  4. extractionextracted with chloroform
  5. dry with materialThe organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customresulting solid
  9. customwas recrystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-248bd4d90f124011af92b2c7075a9ebe
Source dataset
uspto-grants-2009_02
Patent number
US07491734B2

Reaction notes

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