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

HRID 1465992

Reaktionsgleichung

Reaktionsgleichung von HRID 1465992
[ClH:1].[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([CH2:10][C:11](OC1C(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-:37].Cl>CN(C=O)C.C(#N)C>[ClH:1].[CH:4]12[CH2:5][CH2:8][CH:9]([CH2:11][CH2:10]1)[N:2]([CH2:7][C:6]([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:37])[CH2:3]2

Komponenten

7

Edukt 4

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

Produkt 1

HCID 867057762-(3-Azabicyclo[2.2.2]oct-3-yl)-N-(6-bromo-1-benzothien-2-yl)acetamide hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-25b5c426f6b44148a887d9d05fd69497
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09000008B2

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