1,1'-Carbonyldiimidazole → HCID 59716620, compound

Temperature

66 °C

To a solution of 1,1′-carbonyldiimidazole (1.27 g, 7.86 mmol) in THF (20 mL) was added a suspension of 1-(5-(4-fluorophenyl)4-(pyridin-4-yl)pyridazin-3-yl)hydrazine (442 mg, 1.57 mmol) in THF (5 mL). After addition, the reaction mixture was heated to 66° C. After 20 min., the reaction mixture was cooled to RT and the reaction mixture was then concentrated under reduced pressure. The residue was diluted with water. The resultant mixture was extracted with EtOAc (3×100 mL). The combined organic layers were washed with saturated NaCl. The organic layer was dried (Na2SO4), filtered and concentrated. The resulting residue was triturated with EtOAc-hexane to give the title compound, 7-(4-fluorophenyl)-8-(pyridine-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (440 mg, 91%) as a yellow solid. LC/MS (method A): RT=1.27 min, (M+H)+=308.

1. additionAfter addition
2. temperaturethe reaction mixture was cooled to RT
3. concentrationthe reaction mixture was then concentrated under reduced pressure
4. additionThe residue was diluted with water
5. extractionThe resultant mixture was extracted with EtOAc (3×100 mL)
6. washThe combined organic layers were washed with saturated NaCl
7. dry with materialThe organic layer was dried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated
10. customThe resulting residue was triturated with EtOAc-hexane

ORD record

ord-7e961bd28456479597e5c561696cc1ed

Source dataset

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07378418B2