5-Bromothiophene-3-carboxylic acid → HCID 23599495, compound

HRID 1726341Notes

Reaction equation

HRID 1726341 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[S:17][CH:16]=[C:15]([C:18](O)=[O:19])[CH:14]=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[CH:14]=[C:13]([Br:12])[S:17][CH:16]=1)=[O:19])[CH2:4]2

Participants

3

Reactant 2

HCID 120399785-Bromothiophene-3-carboxylic acidHCID 12494972(R)-(+)-3-Aminoquinuclidine Dihydrochloride

Product 1

HCID 23599495HCID 23599495, 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 5-bromothiophene-3-carboxylic acid. The compound was purified by reverse phase HPLC on a Waters Bondapak® C18 column using a gradient of acetonitrile and 0.1% aqueous trifluoroacetic acid as the eluent. The product-containing fractions were evaporated, the residues dissolved in methanol, excess hydrogen chloride solution (4M in 1,4-dioxane) was added and the solution was evaporated. After drying under vacuum, the hydrochloride salt of the title compound was obtained as a colourless solid; MS (ES+) 315, 317 (MH+).

Workup

  1. customPrepared by a method analogous to
  2. customThe compound was purified by reverse phase HPLC on a Waters Bondapak® C18 column
  3. customThe product-containing fractions were evaporated
  4. dissolutionthe residues dissolved in methanol
  5. additionexcess hydrogen chloride solution (4M in 1,4-dioxane) was added
  6. customthe solution was evaporated
  7. customAfter drying under vacuum

Sources & evidence

ORD record
ord-c8cfb86eb88f4287a3dd58e5fa8e3ae1
Source dataset
uspto-grants-2009_02
Patent number
US07491734B2

Reaction notes

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