Acetonitrile → 6-Chloro-4-morpholinopyridazin-3-amine

Temperature

70 °C

4-Bromo-6-chloropyridazin-3-amine (2.0 g, 9.6 mmol) was placed in an 8 mL vial equipped with a stir bar, and ACN (5 mL) and morpholine (8.3 mL, 96 mmol) were added. The mixture was stirred at 70° C. for 18 h. The reaction was cooled to rt, the suspension obtained was filtered, and the filtercake was washed with ACN (10 mL). The filtrate was concentrated under reduced pressure and the residue obtained was dissolved in DCM (50 mL) and washed with saturated NaHCO3 solution (2×30 mL). The aqueous washings were combined and extracted with DCM (3×30 mL). The combined organic extracts were dried over MgSO4 and filtered. The solvent was removed under reduced pressure. The crude residue was triturated with EtOAc (30 mL) then the solid was isolated by filtration to give compound 19a. Mass Spectrum (LCMS, ESI pos.): Calcd. for C8H11ClN4O: 215.1 (M+H). found: 215.1.

1. customvial equipped with a stir bar
2. temperatureThe reaction was cooled to rt
3. customthe suspension obtained
4. filtrationwas filtered
5. washthe filtercake was washed with ACN (10 mL)
6. concentrationThe filtrate was concentrated under reduced pressure
7. customthe residue obtained
8. washwashed with saturated NaHCO3 solution (2×30 mL)
9. extractionextracted with DCM (3×30 mL)
10. dry with materialThe combined organic extracts were dried over MgSO4
11. filtrationfiltered
12. customThe solvent was removed under reduced pressure
13. customThe crude residue was triturated with EtOAc (30 mL)
14. customthe solid was isolated by filtration

ORD record

ord-7ed5e905392e4f9691f18d6f33511fb7

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193736B2