Sodium Hydroxide → HCID 90412792, compound

Temperature

95 °C

[4-Chloro-5-(4-methylpiperazin-1-yl)pyridazin-3-yl]hydrazine (145 mg, 0.5974 mmol) and copper sulfate pentahydrate (522.1 mg, 2.091 mmol) were dissolved in water (9 mL) and stirred at 95° C. for ˜30 minutes. The brown suspension was allowed to cool and 15 wt % NaOH (2 mL) was added. The resulting suspension was heated to 95° C. for ˜5 mins, allowed to cool to RT and filtered through a pre-wetted (10% MeOH in DCM) celite cartridge (10 g). The cartridge was washed with 10% MeOH in DCM and the filtrate was partitioned with water. The aqueous layer was extracted with further 10% MeOH in DCM (3×10 mL) and the combined organics were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (7.5% MeOH/1% NH 40H in DCM, ˜75 mL silica) to give 4-chloro-5-(4-methylpiperazin-1-yl)pyridazine as an off-white solid (100.6 mg, 79% Yield).

1. temperatureto cool
2. temperatureThe resulting suspension was heated to 95° C. for ˜5 mins
3. temperatureto cool to RT
4. filtrationfiltered through a pre-wetted (10% MeOH in DCM) celite cartridge (10 g)
5. washThe cartridge was washed with 10% MeOH in DCM
6. customthe filtrate was partitioned with water
7. extractionThe aqueous layer was extracted with further 10% MeOH in DCM (3×10 mL)
8. dry with materialthe combined organics were dried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customThe residue was purified by column chromatography (7.5% MeOH/1% NH 40H in DCM, ˜75 mL silica)

ORD record

ord-42b6eb08af8447078cec7ae1e087e4da

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08957078B2