HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Triethylamine → Ethyl 2-(2-(3-amino-6-(4-(isopropylsulfonyl)phenyl)pyrazine-2-carbonyl)hydrazinyl)-2-oxoacetate
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Triethylamine | HCID 8471 | — |
| Edukt | Ethoxalyl chloride | HCID 20884 | — |
| Edukt | 3-Amino-6-(4-isopropylsulfonylphenyl)pyrazine-2-carbohydrazide | HCID 59471632 | — |
| Lösungsmittel | Tetrahydrofuran | HCID 8028 | — |
| Produkt | Ethyl 2-(2-(3-amino-6-(4-(isopropylsulfonyl)phenyl)pyrazine-2-carbonyl)hydrazinyl)-2-oxoacetate | HCID 59472330 | 58,5% |
Reaktionsschritte
3-amino-6-(4-isopropylsulfonylphenyl)pyrazine-2-carbohydrazide (2 g, 5.963 mmol) and Et3N (1.810 g, 2.493 mL, 17.89 mmol) were dissolved in THF (128.0 mL) and treated dropwise with ethyl 2-chloro-2-oxo-acetate (814.2 mg, 666.3 μL, 5.963 mmol) at 0° C. The reaction mixture was warmed slowly to room temperature and stirred for 1.5 h. The reaction mixture was filtered and grey solid washed with THF. The filtrate was evaporated to dryness azeotroping with acetonitrile. Then residue was then triturated with acetonitrile to give the product as a yellow solid (1.52 g, 58%); 1H NMR (400 MHZ, DMSO) d 1.19 (m, 6H), 1.32 (m, 3H), 3.34 (m, 1H), 4.32 (m, 2H), 7.88 (m, 2H), 8.56 (m, 2H), 9.07 (s, 1H), 10.95 (s, 1H) and 11.05 (s, 1H) ppm; MS (ES+) 436.32
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08841308B2 |
| Quelldatensatz | uspto-grants-2014_09 |
| ORD ID | ord-4b4f714610f449a0801f1607f809f9fe |
| Quellennotiz | uspto-grants-2014_09 |