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
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
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| Edukt | Dimethylformamide | HCID 6228 | — |
| Edukt | Diisopropylethylamine | HCID 81531 | — |
| Edukt | Methanaminium, 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 Dihydrochloride | HCID 12494972 | — |
| Edukt | 6-Nitro-1-benzofuran-2-carboxylic acid | HCID 13190726 | — |
| Produkt | N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-nitro-1-benzofuran-2-carboxamide | HCID 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
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US08884017B2 |
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| Quelldatensatz | uspto-grants-2014_11 |
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| ORD ID | ord-5f86c9294e3d4456bfa41008dad9777b |
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| Quellennotiz | uspto-grants-2014_11 |
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