Potassium Carbonate → 4-({2-[1-(2-fluorobenzyl)-1H-indazol-3-yl]-5-hydroxypyrimidin-4-yl}amino)pyridine-3-carbonitrile
Reaktionsgleichung
[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]2[N:19]=[C:18]([NH2:20])[C:17]([O:21]C)=[CH:16][N:15]=2)=[N:6]1.C(=O)([O-])[O-].[K+].[K+].Br[C:34]1[CH:39]=[CH:38][N:37]=[CH:36][C:35]=1[C:40]#[N:41]>CN(C)C=O>[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]2[N:19]=[C:18]([NH:20][C:34]3[CH:39]=[CH:38][N:37]=[CH:36][C:35]=3[C:40]#[N:41])[C:17]([OH:21])=[CH:16][N:15]=2)=[N:6]1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
50 mg of 4-amino-2-[1-(2-fluorobenzyl)-1H-indazol-3-yl]pyrimidin-5-ol (1-11-1, 0.149 mmol, 1. eq.) were dissolved in 3 ml of N,N-dimethylformamide. 103 mg of potassium carbonate (0.746 mmol, 5 eq.) and 32.8 mg of 4-bromopyridine-3-carbonitrile (0.179 mmol, 1.2 eq.) were added. The reaction mixture was stirred at 100° C. bath temperature for 18 hours. After cooling at room temperature the mixture was filtered off and washed with dichloromethane. The filtrate was concentrated in vacuo. The residue was purified by preparative HPLC and preparative TLC to yield 4.21 mg (0.01 mmol, 6.1%) of the analytically pure target compound.
Aufarbeitung
- temperatureAfter cooling at room temperature the mixture
- filtrationwas filtered off
- washwashed with dichloromethane
- concentrationThe filtrate was concentrated in vacuo
- customThe residue was purified by preparative HPLC and preparative TLC
- customto yield 4.21 mg (0.01 mmol, 6.1%) of the analytically pure target compound
Quellen und Nachweise
- ORD-Eintrag
- ord-720afc656ec243a5941f741e1c17d91a
- Quelldatensatz
- uspto-grants-2016_02
- Patentnummer
- US09265763B2
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