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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 335590Erstellt: 25. Oktober 2026

Dimethylformamide → N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-nitro-1-benzofuran-2-carboxamide

https://huagongshe.com/reaction/335590

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktDimethylformamideHCID 6228—
EduktDiisopropylethylamineHCID 81531—
EduktMethanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 9886157—
Edukt(R)-(+)-3-Aminoquinuclidine DihydrochlorideHCID 12494972—
Edukt6-Nitro-1-benzofuran-2-carboxylic acidHCID 13190726—
ProduktN-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-nitro-1-benzofuran-2-carboxamideHCID 59341430—

Reaktionsschritte

1040 mg (5.02 mmol) of 6-nitrobenzofuran-2-carboxylic acid, 1000 mg (5.02 mmol) of (R)-3-aminoquinuclidine dihydrochloride, 2290 mg (6.03 mmol) of HATU, 2250 mg (18.08 mmol) of N,N-diisopropylethylamine and 9 ml of DMF are reacted according to the general procedure (variant B). DMF is removed under reduced pressure. The product is taken up in 100 ml of 1N aqueous sodium hydroxide solution and extracted three times with in each case 50 ml of ethyl acetate. The combined organic phases are washed eight times with 1N aqueous sodium hydroxide solution and once with saturated sodium chloride solution and then dried over magnesium sulfate, and the solvent is removed under reduced pressure using a rotary evaporator. 1.34 g (79% of theory) of the title compound are obtained.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08884017B2
Quelldatensatzuspto-grants-2014_11
ORD IDord-5f86c9294e3d4456bfa41008dad9777b
Quellennotizuspto-grants-2014_11