Reaktion #2286301
ord-acd64ba8fbca47659397cb0a99f2264d
Reaktionsgleichung
Edukte
Reagenzien
Lösungsmittel
Reaktionsbedingungen
Aufarbeitung
- 1TemperaturThe reaction mixture was heated to 120° C. for another 24 h
- 2TemperaturThe reaction mixture was cooled to room temperature
- 3Extraktionwas extracted with ether (100 mL)
- 4workup.ADDITIONThe aqueous layer was acidified by the addition of a 1N aqueous hydrochloric acid solution
- 5Extraktionwas extracted with ethyl acetate (2×100 mL)
- 6Waschenwashed with a saturated aqueous sodium chloride solution
- 7Trocknendried with magnesium sulfate
- 8Filtrationfiltered
- 9Einengenconcentrated under vacuum
Vorschrift
A mixture of 2-[3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carbonitrile (31) (136 mg, 0.312 mmol) in glacial acetic acid (3.0 mL) was treated with concentrated hydrochloric acid (0.345 mL). The reaction mixture was heated to 120° C. for 24 h. Starting material was still present by LC/MS. Additional concentrated hydrochloric acid (0.34 mL) was added. The reaction mixture was heated to 120° C. for another 24 h. The reaction mixture was cooled to room temperature and was diluted with water (50 mL). At this time, the reaction was made basic by the addition of a 1N aqueous sodium hydroxide solution and was extracted with ether (100 mL). The organic layer was discarded. The aqueous layer was acidified by the addition of a 1N aqueous hydrochloric acid solution and was extracted with ethyl acetate (2×100 mL). The organic layers were combined, washed with a saturated aqueous sodium chloride solution, dried with magnesium sulfate, filtered and concentrated under vacuum to afford 2-[3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carboxylic acid (32) (111 mg, 78%) as an orange solid which was used without further purification; LRMS for C17H13Cl2N5O6 (M m/z=454. Molecular Weight=454.2291; Exact Mass=453.0243