Water → 6-((S)-sec-Butoxy)-7,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine

HRID 657869

Reaktionsgleichung

[H-].[Na+].Cl[C:4]1[C:5]([CH3:15])=[C:6]([CH3:14])[C:7]2[N:8]([C:10]([NH2:13])=[N:11][N:12]=2)[N:9]=1.[OH2:16]>C[C@H](O)CC.CN(C=O)C>[C@@H:5]([O:16][C:4]1[C:5]([CH3:15])=[C:6]([CH3:14])[C:7]2[N:8]([C:10]([NH2:13])=[N:11][N:12]=2)[N:9]=1)([CH2:6][CH3:7])[CH3:4]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

(S)-Butan-2-ol (1.7 ml) was initially charged at RT with stirring and cooled almost to 0° C. with an ice bath. Subsequently, the mixture was admixed with portions of sodium hydride (85 mg). The suspension formed was heated to 55° C. for 1.5 h and then admixed with portions of 6-chloro-7,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine (W2.006a, 100 mg), suspended in (S)-butan-2-ol (2 ml) and DMF (2 ml). After stirring at 55° C. for 1 h, the mixture was admixed with water and extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate and, after the desiccant had been filtered off, dried under reduced pressure. 105 mg of the title compound were isolated in sufficient purity. LC-MS rt: 0.81 min [M+H]+: 236.2 (met. b)

Aufarbeitung

customThe suspension formed
temperaturewas heated to 55° C. for 1.5 h
stirringAfter stirring at 55° C. for 1 h
extractionextracted three times with dichloromethane
dry with materialThe combined organic phases were dried over sodium sulfate
filtrationafter the desiccant had been filtered off
customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-6c173fa28594464d8c15baef95fe3844
Quelldatensatz: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08076336B2

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