Triethylamine → HCID 18357032, compound

Triethylamine (1.46 ml, 10.5 mmol) and 2-furoyl chloride (1.03 ml, 10.4 mmol) were added to a stirred solution of 1-chloro-4-hydrazinophthalazine hydrochloride (2.0 g, 8.7 mmol) in dioxane (200 ml) at room temperature under nitrogen. The mixture was stirred at room temperature for 2 h and then heated at reflux for 6 h. The mixture was cooled to room temperature, the solvent evaporated in vacuo and the residue partitioned between dichloromethane (800 ml) and water (200 ml). The organic layer was separated, washed further with water (4×200 ml) and brine (x 1), dried (MgSO4) and evaporated in vacuo. The residue was chromatographed on silica gel, eluting with a 0.5-2% methanol/dichloromethane gradient, to afford the title-product (0.665 g, 28%); 1H NMR (250 MHz, CDCl3) 6.68 (1H, q, J=1.7 Hz, Ar—H), 7.56 (1H, m, Ar—H), 7.73 (1H, m, Ar—H), 7.91 (1H, m, Ar—H), 8.05 (1H, m, Ar—H), 8.31 (1H, d, J=7.5 Hz, Ar—H), 8.76 (1H, m, Ar—H).

1. temperatureheated
2. temperatureat reflux for 6 h
3. temperatureThe mixture was cooled to room temperature
4. customthe solvent evaporated in vacuo
5. customthe residue partitioned between dichloromethane (800 ml) and water (200 ml)
6. customThe organic layer was separated
7. washwashed further with water (4×200 ml) and brine (x 1)
8. dry with materialdried (MgSO4)
9. customevaporated in vacuo
10. customThe residue was chromatographed on silica gel
11. washeluting with a 0.5-2% methanol/dichloromethane gradient

ORD record

ord-1950a3be517848dd9c135e73110a7da0

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06313125B1