Reaktionsgleichung
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][C:3]=1[CH3:12].[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]2[CH:20]=[CH:21][C:22]([NH2:25])=[N:23][CH:24]=2)[N:14]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.CN(C=O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([NH:25][C:22]2[CH:21]=[CH:20][C:19]([C:15]3[N:14]=[N:13][CH:18]=[CH:17][CH:16]=3)=[CH:24][N:23]=2)=[O:11])=[CH:4][C:3]=1[CH3:12]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A mixture of 2-(6-chloro-5-methylpyridin-3-yl)acetic acid 86-7 (241 mg, 1.3 mmol), 5-(pyridazin-3-yl)pyridin-2-amine 145-3 (224 mg, 1.3 mmol), 1,3-dicyclohexylcarbodiimide (325 mg, 1.6 mmol) and 4-(dimethylamino)pyridine (26 mg, 0.26 mmol) in DMF (6 mL) was stirred at room temperature for 10 hours. The reaction mixture was filtered to remove the solid and the filtrate was diluted with ethyl acetate, washed with water and brine, dried over Na2SO4 and concentrated to dryness by rotary evaporation. The crude product was purified by silica gel flash chromatography, eluted with 5% methanol in dichloromethane to give 2-((6-chloro-5-methylpyridin-3-yl)-N-(5-(pyridazin-3-yl)pyridin-2-yl)acetamide 145-4 as pale yellow solid. MS m/z 340.2 (M+1)
Aufarbeitung
- filtrationThe reaction mixture was filtered
- customto remove the solid
- additionthe filtrate was diluted with ethyl acetate
- washwashed with water and brine
- dry with materialdried over Na2SO4
- concentrationconcentrated to dryness by rotary evaporation
- customThe crude product was purified by silica gel flash chromatography
- washeluted with 5% methanol in dichloromethane
Quellen und Nachweise
- ORD-Eintrag
- ord-6e61d1d256ec4951bebcd85450e3002c
- Quelldatensatz
- uspto-grants-2016_01
- Patentnummer
- US09238646B2
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