HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Diisopropylethylamine → 4-[2-(5-Bromo-pyridin-2-yloxy)-acetylamino]-thiophene-3-carboxylic acid methyl ester
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Diisopropylethylamine | HCID 81531 | — |
| Edukt | 2-[(5-Bromopyridin-2-yl)oxy]acetic acid | HCID 302912 | — |
| Edukt | Methyl 4-aminothiophene-3-carboxylate Hydrochloride | HCID 2777609 | — |
| Edukt | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Lösungsmittel | Water | HCID 962 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | 4-[2-(5-Bromo-pyridin-2-yloxy)-acetylamino]-thiophene-3-carboxylic acid methyl ester | HCID 68691710 | 73% |
Reaktionsschritte
To a solution of methyl 4-amino-3-thiophenecarboxylate hydrochloride (500 mg, 2.58 mmol) in dimethylformamide (25 mL) was added N-ethyldiisopropylamine (2.26 mL, 12.9 mmol), (5-bromo-pyridin-2-yloxy)-acetic acid ([79674-66-1], 600 mg, 2.58 mmol) and HATU (1.24 g, 3.23 mmol). The reaction mixture was allowed to stir for 2 hours at room temperature. After such time, water was added, and precipitation was eased by ultrasonication. The precipitate was isolated by filtration and washed with a mixture of water and ethanol (3:1) to yield 4-[2-(5-bromo-pyridin-2-yloxy)-acetylamino]-thiophene-3-carboxylic acid methyl ester (699 mg, 73%) as a light brown solid.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US07732452B2 |
| Quelldatensatz | uspto-grants-2010_06 |
| ORD ID | ord-602983a549b047a1bb2106f55a85107c |
| Quellennotiz | uspto-grants-2010_06 |