HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Acetonitrile → 2-amino-5-(3-cyclopropylsulfamoyl-phenyl)-N-methoxy-N-methyl-nicotinamide
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Acetonitrile | HCID 6342 | — |
| Edukt | Dichloromethane | HCID 6344 | — |
| Edukt | (3-(N-Cyclopropylsulfamoyl)phenyl)boronic acid | HCID 44119335 | — |
| Edukt | 2-amino-5-bromo-N-methoxy-N-methylnicotinamide | HCID 59699724 | — |
| Katalysator | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Lösungsmittel | Water | HCID 962 | — |
| Lösungsmittel | 1,2-Dimethoxyethane | HCID 8071 | — |
| Lösungsmittel | Sodium Carbonate | HCID 10340 | — |
| Produkt | 2-amino-5-(3-cyclopropylsulfamoyl-phenyl)-N-methoxy-N-methyl-nicotinamide | HCID 86634544 | — |
Reaktionsschritte
A suspension of 2-Amino-5-bromo-N-methoxy-N-methyl-nicotinamide (0.2 g, 0.77 mmol), N-cyclopropyl 3-boronobenzenesulfonamide (0.2 g, 0.84 mmol), Pd(dppf)Cl2.DCM (0.063 g, 0.077 mmol) in 2M Na2CO3 (1 ml) and DME (3 ml) is heated at reflux for 1 hour. The crude reaction mixture is subjected to column chromatography (Isolute™ C18, 0-100% MeCN in water −0.1% TFA). All the acetonitrile is removed in vacuo, and the aqueous solution remaining is adjusted to basic pH using NaHCO3. The product is extracted into DCM, and dried (MgSO4). Concentration and drying in vacuo at 40° C. yields the title compound. [M+H]+ 726
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08268834B2 |
| Quelldatensatz | uspto-grants-2012_09 |
| ORD ID | ord-0f769ef43d8646fbb8191300db62f2a9 |
| Quellennotiz | uspto-grants-2012_09 |