HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Diisopropylethylamine → (R)-N-(3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)-2-(2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxamide
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| 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 | HCID 58552948 | HCID 58552948 | — |
| Edukt | 2-(2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid | HCID 67201602 | — |
| Lösungsmittel | Water | HCID 962 | — |
| Lösungsmittel | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Produkt | (R)-N-(3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)-2-(2-(trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxamide | HCID 67203479 | — |
Reaktionsschritte
2-(2-(Trifluoromethyl)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid (3; 75 mg, 0.24 mmol) was taken up in NMP (2 mL) along with (R)-3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)aniline (133; 64.3 mg, 0.288 mmol) and HATU (186 mg, 0.49 mmol). DIEA (81 μL, 0.49 mmol) was added and the resulting reaction mixture was stirred at room temperature for 12 h. The temperature was then raised to 60° C. and the reaction mixture was allowed to stir for an additional 1 h. The reaction mixture was diluted with water and filtered. The collected solids were further purified by silica gel chromatography to afford the desired product 134, as a yellow solid (51.5 mg, 42%).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08846947B2 |
| Quelldatensatz | uspto-grants-2014_09 |
| ORD ID | ord-930a91f7a1494d79b2bed38bf4945ef7 |
| Quellennotiz | uspto-grants-2014_09 |