4-Benzhydryl-1-piperazinepropanol → 6-[3-[4-(Diphenylmethyl)piperazino]propoxy]-7-isopropyl[1,2,4]triazolo[1,5-b]pyridazine dihydrochloride

4-(Diphenylmethyl)-1-piperazinepropanol (466 mg) was dissolved in dried tetrahydrofuran (10 ml), followed by addition of sodium t-butoxide (173 mg). The mixture was refluxed under heating for 30 minutes. After the mixture was cooled, 6-chloro-7-isopropyl[1,2,4]triazolo[1,5-b]pyridazine (295 mg) was added thereto. The resulting mixture was refluxed for 3 hours under heating. After cooling, ice-water was added to the mixture, followed by extraction with ethyl acetate. The extract was washed with an aqueous sodium chloride saturated solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with a mixture of ethyl acetate and methanol (10:1). Fractions containing the objective compound were collected and dissolved in ethanol (10 ml), followed by addition of 1N-HCl (3 ml). The mixture was concentrated under reduced pressure. The resulting crystals were recrystalized from ethyl acetate to yield the title compound (582 mg).

1. temperatureThe mixture was refluxed
2. temperatureunder heating for 30 minutes
3. temperatureAfter the mixture was cooled
4. temperatureThe resulting mixture was refluxed for 3 hours
5. temperatureunder heating
6. temperatureAfter cooling
7. extractionfollowed by extraction with ethyl acetate
8. washThe extract was washed with an aqueous sodium chloride saturated solution
9. dry with materialdried over magnesium sulfate
10. concentrationconcentrated under reduced pressure
11. washeluted with a mixture of ethyl acetate and methanol (10:1)
12. additionFractions containing the objective compound
13. customwere collected
14. dissolutiondissolved in ethanol (10 ml)
15. additionfollowed by addition of 1N-HCl (3 ml)
16. concentrationThe mixture was concentrated under reduced pressure
17. customThe resulting crystals were recrystalized from ethyl acetate

ORD 기록

ord-efb4ee823bb746b4ba6b8e0cef3d9971

출처 데이터셋

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06248740B1