Réaction #84052

Équation de réaction

6-bromo-1-benzothiophene-2-amine

pentafluorophenyl (1-azabicyclo[2.2.2]oct-3-yl)acetate hydrochloride

hydrochloric acid

carbonate

→

title compound

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

Solvants

DMF

acetonitrile

Conditions de réaction

Traitement

1. 1
   workup.WAITAfter 3 h
2. 2
   Filtrationthe polystyrene resin is filtered off
3. 3
   Lavagewashed with THF
4. 4
   ConcentrationThe combined filtrates are concentrated in vacuo
5. 5
   Autrethe crude product is purified by preparative HPLC
6. 6
   AutreThe hydrochloride is prepared
7. 7
   workup.ADDITIONby mixing the product
8. 8
   Concentrationagain concentrating
9. 9
   AutreDrying under high vacuum

Mode opératoire

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.

Source