Sodium hydride → [6-(6-Chloro-imidazo[1,2-b]pyridazin-8-ylamino)-pyridin-3-yl]-morpholin-4-yl-methanone
Reaktionsgleichung
Br[C:2]1[C:3]2[N:4]([CH:9]=[CH:10][N:11]=2)[N:5]=[C:6]([Cl:8])[CH:7]=1.[NH2:12][C:13]1[N:18]=[CH:17][C:16]([C:19]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[O:20])=[CH:15][CH:14]=1.[H-].[Na+]>CN(C=O)C>[Cl:8][C:6]1[CH:7]=[C:2]([NH:12][C:13]2[N:18]=[CH:17][C:16]([C:19]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[O:20])=[CH:15][CH:14]=2)[C:3]2[N:4]([CH:9]=[CH:10][N:11]=2)[N:5]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
A mixture of 8-bromo-6-chloroimidazo[1,2-b]pyridazine (272 mg, 1.17 mmol, Eq: 1.00) and (6-aminopyridin-3-yl)(morpholino)methanone (255 mg, 1.23 mmol, Eq: 1.05) in DMF (10.0 ml) was cooled to 0° C. To this reaction mixture was added sodium hydride (150 mg, (60% in mineral oil), 3.74 mmol, Eq: 3.2). The reaction was allowed to stir at 0° C. for 10 minutes and then allowed to warm to room temperature and stir 18 h. The reaction mixture was quenched with sat. NaHCO3 (aq) and diluted with water and EtOAc. An insoluble solid was collected by filtration to give [6-(6-chloro-imidazo[1,2-b]pyridazin-8-ylamino)-pyridin-3-yl]-morpholin-4-yl-methanone (420 mg, 99%). LC/MS-ESI observed [M+H]+ 358.
Aufarbeitung
- temperatureto warm to room temperature
- stirringstir 18 h
- customThe reaction mixture was quenched with sat. NaHCO3 (aq)
- additiondiluted with water and EtOAc
- filtrationAn insoluble solid was collected by filtration
Quellen und Nachweise
- ORD-Eintrag
- ord-d3dbf29455954ae3a7d53f501695c330
- Quelldatensatz
- uspto-grants-2014_06
- Patentnummer
- US08742098B2
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