HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Diisopropylethylamine → 2-acetamido-N-((4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methyl)isonicotinamide
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Diisopropylethylamine | HCID 81531 | — |
| Edukt | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Edukt | 2-Acetamidopyridine-4-carboxylic acid | HCID 3774466 | — |
| Edukt | (4-(2,2,2-Trifluoroethoxy)pyridin-2-yl)methanamine dihydrochloride | HCID 67510820 | — |
| Lösungsmittel | Water | HCID 962 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | 2-acetamido-N-((4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methyl)isonicotinamide | HCID 56966008 | 38% |
Reaktionsschritte
To a mixture of (4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methanamine dihydrochloride (20 mg, 0.070 mmol, Amine-2), 2-acetamidoisonicotinic acid (15 mg, 0.084 mmol) and N,N-diisopropylethylamine (0.049 mL, 0.28 mmol) in N,N-dimethylformamide (0.5 mL) is added a solution of HBTU (40 mg, 0.11 mmol) in N,N-dimethylformamide (0.5 mL) at room temperature. After stirring at room temperature for 2 hours, the mixture is poured into water (2 mL) and extracted with ethyl acetate (3 mL). The organic layer is dried over sodium sulfate and concentrated under reduced pressure. The residue is purified by column chromatography on NH-silica gel eluting with ethyl acetate and then by preparative LC-MS to give 9.8 mg (38% yield) of the title compound.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US09302991B2 |
| Quelldatensatz | uspto-grants-2016_04 |
| ORD ID | ord-29829bd2666844e5b2e0022e1a8989de |
| Quellennotiz | uspto-grants-2016_04 |