1-[2-Chloro-1-hydroxy-3-(6-quinolinyl)propyl]-2,5-pyrrolidinedione → Methyl 2-chloro-4-[7-(quinolin-6-ylmethyl)imidazo[1,2-b][1,2,4]triazin-2-yl]benzoate
Reaktionsgleichung
[NH2:1][C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([Cl:18])[CH:9]=2)=[CH:6][N:7]=1.Cl[CH:20]([CH2:30][C:31]1[CH:32]=[C:33]2[C:38](=[CH:39][CH:40]=1)[N:37]=[CH:36][CH:35]=[CH:34]2)[CH:21](N1C(=O)CCC1=O)O>C(O)CCC>[Cl:18][C:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[N:7][C:2]3[N:3]([C:20]([CH2:30][C:31]4[CH:32]=[C:33]5[C:38](=[CH:39][CH:40]=4)[N:37]=[CH:36][CH:35]=[CH:34]5)=[CH:21][N:1]=3)[N:4]=2)[CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 110 °C
Versuchsvorschrift
The mixture of methyl 4-(3-amino-1,2,4-triazin-6-yl)-2-chlorobenzoate (Step 2, 0.840 g, 3.17 mmol) and 1-(2-chloro-1-hydroxy-3-quinolin-6-ylpropyl)pyrrolidine-2,5-dione (1.11 g, 3.49 mmol, Example 1, Step 7) in 1-butanol (11.6 mL) was stirred at 110° C. for 22 h. The solvent was removed under reduced pressure. The residue was triturated with ethyl acetate. The precipitate was collected by filtration and washed with ethyl acetate and hexane to yield the desired product (0.908 g). The mother liquor was concentrated to half volume. The precipitate was collected by filtration and washed with ethyl acetate and hexane to afford additional desired product (0.342 g). The total product obtained was 1.10 g (80.6%). LCMS (M+H)+: m/z=430.0/431.9.
Aufarbeitung
- customThe solvent was removed under reduced pressure
- customThe residue was triturated with ethyl acetate
- filtrationThe precipitate was collected by filtration
- washwashed with ethyl acetate and hexane
Quellen und Nachweise
- ORD-Eintrag
- ord-f84bddcbb4db4fbaa710bbb2d43cdbe2
- Quelldatensatz
- uspto-grants-2013_07
- Patentnummer
- US08487096B2
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