Hydrochloric Acid → 2-(1-Azabicyclo[2.2.2]oct-3-yl)-N-(6-bromo-1-benzothien-2-yl)acetamide hydrochloride

HRID 1896492

Reaction equation

HRID 1896492 reaction equation
[ClH:1].[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([CH2:10][C:11]([O:13]C1C(F)=C(F)C(F)=C(F)C=1F)=O)[CH2:3]2.[Br:25][C:26]1[CH:35]=[CH:34][C:29]2[CH:30]=[C:31]([NH2:33])[S:32][C:28]=2[CH:27]=1.C(=O)([O-])[O-].Cl>CN(C=O)C.C(#N)C>[ClH:1].[N:2]12[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9]1)[CH:4]([CH2:10][C:11]([NH:33][C:31]1[S:32][C:28]3[CH:27]=[C:26]([Br:25])[CH:35]=[CH:34][C:29]=3[CH:30]=1)=[O:13])[CH2:3]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 19660Carbonate IonHCID 179798236-Bromobenzo[b]thiophen-2-amineHCID 86610796Pentafluorophenyl (1-azabicyclo[2.2.2]oct-3-yl)acetate hydrochloride

Product 1

HCID 179798252-(1-Azabicyclo[2.2.2]oct-3-yl)-N-(6-bromo-1-benzothien-2-yl)acetamide hydrochloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

89.2 mg (0.24 mmol) of pentafluorophenyl (1-azabicyclo[2.2.2]oct-3-yl)acetate hydrochloride are dissolved in 1 ml of DMF, mixed with 71.2 mg (0.31 mmol) of 6-bromo-1-benzothiophene-2-amine and stirred at room temperature overnight. 1 g of MP-carbonate (polymer-bound carbonate, capacity: 2.5-3.5 mmol/g; from Argonaut Technologies, USA) is added. After 3 h, the polystyrene resin is filtered off and washed with THF. The combined filtrates are concentrated in vacuo, and the crude product is purified by preparative HPLC. The hydrochloride is prepared by mixing the product with a mixture of 1 M hydrochloric acid and acetonitrile and again concentrating. Drying under high vacuum results in 14 mg (14% of theory) of the title compound.

Workup

  1. waitAfter 3 h
  2. filtrationthe polystyrene resin is filtered off
  3. washwashed with THF
  4. concentrationThe combined filtrates are concentrated in vacuo
  5. customthe crude product is purified by preparative HPLC
  6. customThe hydrochloride is prepared
  7. additionby mixing the product
  8. concentrationagain concentrating
  9. customDrying under high vacuum

Sources & evidence

ORD record
ord-5640154e8dad429e9127d6173e8b8aaa
Source dataset
uspto-grants-2013_08
Patent number
US08518967B2

Linked notes

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