Reaktion #43727

Reaktionsgleichung

3-chloro-6-nitro-1-benzothiophene-2-carboxylic acid

HATU

N,N-diisopropylethylamine

DMF

→

title compound

N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-3-chloro-6-nitro-1-benzothiophene-2-carboxamide

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe mixture is filtered
2. 2
   Waschenwashed successively with water, methanol, methanol/trifluoroacetic acid 9:1 and methanol/trifluoroacetic acid 1:1
3. 3
   SonstigeEvaporation of the filtrate

Vorschrift

427 mg (1.66 mmol) of 3-chloro-6-nitro-1-benzothiophene-2-carboxylic acid, 300 mg (1.51 mmol) of R-3-aminoquinuclidine dihydrochloride, 687.4 mg (1.81 mmol) of HATU, 701 mg (5.43 mmol) of N,N-diisopropylethylamine and 4.0 ml of DMF are reacted according to the general procedure. 20 ml of methanol and 4 g of Dowex WX2-200 are added, and the mixture is stirred at RT for 1 h. The mixture is filtered and washed successively with water, methanol, methanol/trifluoroacetic acid 9:1 and methanol/trifluoroacetic acid 1:1. Evaporation of the filtrate gives 270 mg (49% of theory) of the title compound.

Quelle