1,2-Dichloroethane → N-[(3S)-1-Azabicyclo[2.2.2]oct-3-yl]-7-bromo-1-benzothiophene-2-carboxamide hydrochloride

HRID 2179580Notes

Reaction equation

HRID 2179580 reaction equation
C(Cl)C[Cl:3].C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[Br:22][C:23]1[C:31]2[S:30][C:29]([C:32]([OH:34])=O)=[CH:28][C:27]=2[CH:26]=[CH:25][CH:24]=1.Cl.Cl.[NH2:37][C@H:38]1[CH:43]2[CH2:44][CH2:45][N:40]([CH2:41][CH2:42]2)[CH2:39]1.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[ClH:3].[N:40]12[CH2:45][CH2:44][CH:43]([CH2:42][CH2:41]1)[C@H:38]([NH:37][C:32]([C:29]1[S:30][C:31]3[C:23]([Br:22])=[CH:24][CH:25]=[CH:26][C:27]=3[CH:28]=1)=[O:34])[CH2:39]2

Participants

9

Reactant 6

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 12494973(3S)-1-azabicyclo[2.2.2]octan-3-amine dihydrochlorideHCID 179795837-Bromo-1-benzothiophene-2-carboxylic acid

Product 1

HCID 67313990N-[(3S)-1-Azabicyclo[2.2.2]oct-3-yl]-7-bromo-1-benzothiophene-2-carboxamide hydrochloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3.58 g (18.7 mmol) of EDC, 2.52 g (18.7 mmol) of HOBt and 7.8 ml (56 mmol) of triethylamine are added to a solution, cooled to 0° C., of 4.0 g (15.6 mmol) of 7-bromo-1-benzothiophene-2-carboxylic acid (Example 7A) and 3.10 g (15.6 mmol) of (S)-3-aminoquinuclidine dihydrochloride in 50 ml of DMF. The mixture is stirred at room temperature for 18 h. The reaction is stopped by adding 10% strength sodium bicarbonate solution. The precipitate resulting after addition of ethyl acetate is filtered off. The aqueous phase is extracted with ethyl acetate, the combined organic phases are dried over sodium sulphate and concentrated, and the residue is dried under high vacuum. 4.70 g (68% of theory) of the title compound are obtained.

Workup

  1. customThe precipitate resulting
  2. filtrationis filtered off
  3. extractionThe aqueous phase is extracted with ethyl acetate
  4. dry with materialthe combined organic phases are dried over sodium sulphate
  5. concentrationconcentrated
  6. customthe residue is dried under high vacuum

Sources & evidence

ORD record
ord-e1842168e9084fbfa28fb289e3d515bb
Source dataset
uspto-grants-2015_06
Patent number
US09067931B2

Reaction notes

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