Reaktionsgleichung
C([C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([C:12]([O-:14])=O)=[CH:10][N:11]=2)[CH:8]=1)#N.[Li+].ClC1C=C(Cl)C=C(Cl)C=1C(Cl)=O.[CH2:28]([C:30]1[C:38]2[C:37]([NH2:39])=[CH:36][CH:35]=[CH:34][C:33]=2[N:32]([CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[C:43]([CH3:47])[N:42]=2)[N:31]=1)[CH3:29].C(=O)(O)[O-].[Na+].[CH3:53][N:54]1C(=O)CCC1>>[C:53]([C:10]1[N:11]=[C:6]2[CH:5]=[CH:4][CH:3]=[CH:8][N:7]2[C:9]=1[C:12]([NH:39][C:37]1[CH:36]=[CH:35][CH:34]=[C:33]2[C:38]=1[C:30]([CH2:28][CH3:29])=[N:31][N:32]2[CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[C:43]([CH3:47])[N:42]=1)=[O:14])#[N:54]Komponenten
Edukt 5
Produkt 1
Versuchsvorschrift
Lithium 6-cyanoimidazo[1,2-a]pyridine-3-carboxylate (107 mg, 0.6 mmol) was dissolved in anhydrous NMP (2.8 mL) and 2,4,6-trichlorobenzoyl chloride (94 mL, 0.6 mmol) was added dropwise. The mixture was stirred at ambient temperature for 30 minutes. 3-Ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-amine (137 mg, 0.5 mmol) was added in one portion and the reaction mixture was heated to 80° C. for 6 hours. Saturated sodium bicarbonate solution was added until a precipitate formed and the mixture was allowed to stir at ambient temperature for 1 hour. The precipitate was collected by filtration and dried under high vacuum for 2 hours to give cyano-N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide as a beige solid (147 mg). MS m/z 436.3 (M+1, APCI+).
Aufarbeitung
- temperaturethe reaction mixture was heated to 80° C. for 6 hours
- customformed
- stirringto stir at ambient temperature for 1 hour
- filtrationThe precipitate was collected by filtration
- customdried under high vacuum for 2 hours
Quellen und Nachweise
- ORD-Eintrag
- ord-270647247a5b43c4aea27b8cc7ddcf68
- Quelldatensatz
- uspto-grants-2014_09
- Patentnummer
- US08841455B2
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