3-Chloro-6-hydrazinopyridazine

Intermediate L6-((6-Chloro-[1 , 2, 4]triazolo[4, 3-b]pyridazin-3-yl)methyl)quinoline Acetic acid, 50A solution of 3, 6-dichloropyridazine (3g, 20.14 mmol) and hydrazine monohydrate (1 g, 20.14 mmol) in 20 ml_ THF in a sealed tube was heated at 80 To a solution of 3, 6-dichloropyridazine (20 g, 134 mmol) in ethanol (175 mL) was added hydrazine hydrate (23 mL, 0.47 mol) and NHDissolve 3, 6-dichloropyridazine (20 g, 134 mmol) in ethanol (175 mL), add hydrazine hydrate (23 mL, 469 mmol) and NH4OH (30 mL), reflux at 80 ° C for 30 minutes , And the reaction solution was refrigerated for 15 hours. The resulting solid was crystallized with ether and filtered to give 1- (6-chloropyridazin-3-yl) hydrazine (14 g, 100percent).3-chloro-6-hydrazinylpyridazine Synthesis of S-chloro-6-hydrazinylpyridazine To a degassed solution of 3, 6-dichloropyridazine (18 g, 120 mmol) and hydrazine (6.4 mL) in 1, 4-dioxane (80 mL) was added EtTo a 1000 mL single-necked round bottom flask was added 3, 6-dichloropyridazine (29.80 g, 200 mmol), hydrazine hydrate (15.00 g, 300 mmol), DMF and acetonitrile (280 ml of DMF). The reaction mixture was stirred at 90 °C for 10 hours. TLC and GC were determined to complete the reaction. After the reaction, the solvent was removed by steaming, get the crude product, the pure product was isolated by silica gel column chromatography 3-chloro-6-hydrazinopyridazine, after drying, the calculated yield was 83.65percent. Purity 98.69percent (HPLC).3, 6-Dichloropyridazine (1 eq) was dissolved in tetrahydrofuran (0.33 mol/L), then potassium carbonate (0.1 eq) and hydrazine monohydrate (1 .6 eq) were added. The reaction mixture was heated to reflux for 48 hours. The reaction mixture was evaporated to half volume, and hydrazine monohydrate (1 eq) was added to the residue. The mixture was stirred overnight at reflux. The hot suspension was filtered. The filtrate was cooled to 0°C and filtered. The filtrate was concentrated and it was cooled at 0°C, the solid was filtered, to give Intermediate A (75percent yield). Appearance: off-white solid. INTERMEDIATE 1(6-Chloropyridazin-3 -yl)hydrazineA stirred solution of 3, 6-dichloropyridazine (3.0 g, 20.3 mmol) and hydrazine hydrate (0.97 g, 20.3 mmol) in THF (15 mL) was heated at 80°C for 12 h in a sealed tube.The reaction mixture was concentrated in vacuo. The crude residue was triturated with Et20 to give the title compound (2.0 g, 68percent), which was used without further purification. H (400 MHz, DMSO-d6) 8.25 (s, 1H), 7.42 (dd, 1H, J9.5, 1.6 Hz), 7.10 (d, 1H, J9.4 Hz), 4.99-4.10 (m, 2H).(a) a)

Molecular Weight:144.56
XLogP3:0.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:144.0202739
Monoisotopic Mass:144.0202739
Topological Polar Surface Area:63.8
Heavy Atom Count:9
Complexity:88.6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes