HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Dichloromethane → 5-(5-bromo-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)-N-(2-(dimethylamino)ethyl)thiophene-2-sulfonamide
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Dichloromethane | HCID 6344 | — |
| Edukt | 2,5-dibromo-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine | HCID 58169191 | — |
| Edukt | N-(2-(dimethyl amino)ethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-sulfonamide | HCID 66927474 | — |
| Katalysator | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Lösungsmittel | Sodium Carbonate | HCID 10340 | — |
| Lösungsmittel | 1,4-Dioxane | HCID 31275 | — |
| Produkt | 5-(5-bromo-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)-N-(2-(dimethylamino)ethyl)thiophene-2-sulfonamide | HCID 58169502 | 20% |
Reaktionsschritte
A mixture of Pd(dppf)Cl2.CH2Cl2 (182 mg, 0.22 mmol, 0.1 equiv.), the crude N-(2-(dimethyl amino)ethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-sulfonamide and 2,5-dibromo-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine (700 mg, 1.95 mmol, 1.0 eq) in dioxane (20 mL) and saturated Na2CO3 aqueous (2 mL) was heated at 100° C. for 2 h under nitrogen atmosphere. The reaction mixture was cooled to room temperature, and extracted with THF. The combined organic layers were purified by silica gel chromatography to afford compound 5-(5-bromo-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)-N-(2-(dimethylamino)ethyl)thiophene-2-sulfonamide (200 mg, 20% over 2 steps). LC-MS (m/z)=512.0, 514.0 [M+H]+.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US09422271B2 |
| Quelldatensatz | uspto-grants-2016_08 |
| ORD ID | ord-018d8829acaf4c8e8ef5ed5e56c5a5f8 |
| Quellennotiz | uspto-grants-2016_08 |