HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Cesium carbonate → 1-[4-[2-(Isoquinolin-3-ylamino)-pyridin-4-ylmethyl]-piperazin-1-yl]-ethanone
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Cesium carbonate | HCID 10796 | — |
| Edukt | Isoquinolin-3-Amine | HCID 311869 | — |
| Edukt | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Edukt | 1-(2-Chloropyridin-4-ylmethyl)-4-acetylpiperazine | HCID 58285182 | — |
| Katalysator | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Lösungsmittel | Toluene | HCID 1140 | — |
| Lösungsmittel | Ethyl Acetate | HCID 8857 | — |
| Produkt | 1-[4-[2-(Isoquinolin-3-ylamino)-pyridin-4-ylmethyl]-piperazin-1-yl]-ethanone | HCID 44612470 | — |
Reaktionsschritte
1-(2-Chloropyridin-4-ylmethyl)-4-acetylpiperazine (1.0 equiv) (Preparation B-15) was mixed with 3-aminoisoquinoline (1.0 equiv), Pd2(dba)3(0.1 equiv), xantphos (0.15 equiv), and Cs2CO3 (1.4 equiv) in toluene. The mixture was refluxed overnight, and EtOAc was added in to dilute the mixture. After filtration, the filtrate was concentrated and applied onto a silica gel column. The title compound was obtained as a yellow solid (50 mg, yield 48%). 1H NMR (CDCl3, 300 MHz) δ: 2.10 (s, 3H, Ac), 2.47 (t, J=4.1 Hz, 4H, PyCH2NCH2CH2), 3.58 (dt, J=4.8 Hz, 50.7 Hz, 4H, NCH2CO), 3.60 (s, 2H, pyridylCH2), 6.86-8.99 (m, 9H, isoquinolyl+pyridyl).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08461339B2 |
| Quelldatensatz | uspto-grants-2013_06 |
| ORD ID | ord-4e4cae14340f4d6fb08ae527b6bbb156 |
| Quellennotiz | uspto-grants-2013_06 |