3-Pyridazinamine

White to yellow to light brown powder or crystal

4-(3-Phenyl-1, 2, 4-thiadiazol-5-yl)-N-pyridazine-1-carboxamide; (1) Pyridazine-3-amine; A mixture of 6-chloropyridazine-3-amine (5.00 g, 38.6 mmol), tetrahydrofuran (240 ml), sodium hydroxide (8.00 g, 200 mmol), water (32 ml) and 10percent palladium-carbon (500 mg) was stirred under a hydrogen atmosphere at room temperature for 2 days, insolubles were filtered off and the filtrate was concentrated. The residue was dissolved in methanol (100 ml), insolubles were filtered off and the filtrate was concentrated to obtain the desired product as a solid quantitatively. To a solution of 2 (875 mg, 6.76 mmol) and sodium hydroxide(304 mg, 6.76 mmol) in absolute ethanol (30 mL) stirred underargon was added Pd/C (131 mg, 1.23 mmol). The mixture was thenstirred at room temperature under hydrogen atmosphere and reaction progress was followed by TLC monitoring. After 20 h, themixture was filtered through a celite pad and the filtrate wasevaporated under reduced pressure. The crude product waswashed with Et2O to give compound 30 (700 mg, 100percent) as a palepink solid.Mp 164.1 C. 1H NMR (300 MHz, CDCl3) d 8.58 (dd, 1H, J 4.5, 1.5 Hz, H6), 7.23 (dd, 1H, J 9.0, 4.5 Hz, H5), 6.83 (dd, 1H, J 9.0, 1.5 Hz, H4), 5.18 (bs, 2H, NH2). 13C NMR (75 MHz, CDCl3) d 159.5, 144.1, 128.2, 114.6.Example 23Synthesis of 4-[2-(difluoromethyl)-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(3-pyridazinyl)-1, 3, 5-triazin-2-amineThe compound was synthesized according to Method A.A mixture of 0.063 g (0.486 mmol) of 6-chloro-3-pyridazinamine (J. Med. Chem. 2006, 49, 4409-4424), 0.022 g (0.55 mmol) of NaOH, and 0.045 g of 10percent Pd/C in ethanol (15 mL) was stirred under an atmosphere of hydrogen for 18 hrs. After filtration through celite, the solvent was concentrated to give 0.046 g (99.5percent yield) of 3-aminopyridazine: Example 39; Synthesis of 4-(3-(5-cyclopropylpyridin-2-yloxy)benzylidene)-N-(pyridazin-3-yl)piperidine-1-carboxamide; Step 1; Pyridazin-3-amine; To a solution of 6-chloropyridazin-3-amine (19.2 g, 148 mmol) in EtOH (500 mL) was added 10percent Pd catalyst on 1940 carbon (unreduced, 55percent water). Triethylamine (50 mL) was added and the mixture was hydrogenated under 500 psi/mole for 1.9 h. The reaction was filtered and the ethanol was washed with aqueous NHSynthesis of Phenyl pyridazin-3-ylcarbamate; To a solution of 3-amino-6-chloropyridazine (19.2 g, 148 mmol; CAS No.5469-69-2) in EtOH (500 mL) was added 10percent Pd catalyst on 1940 carbon (unreduced, 55percent water). Triethylamine (50 mL) was added and the mixture was hydrogenated under 500 psi/mole for 1.9 h. The reaction was filtered and the ethanol was washed with aqueous NHPhenyl pyridazin-3-ylcarbamateTo a solution of 3-amino-6-chloropyridazine (19.2 g, 148 mmol; CASNo. 5469-69-2) in EtOH (500 mL) was added 10percent Pd catalyst on 1940 carbon (unreduced, 55percent water). Triethylamine (50 mL) was added and the mixture was hydrogenated under 500 psi/mole for 1.9 h. The reaction was filtered and the ethanol was washed with aqueous NHTo a solution of 3-amino-6-chloropyridazine (19.2 g, 148 mmol; CASNo. 5469-69-2) in EtOH (500 mL) was added 10percent Pd catalyst on 1940 carbon (unreduced, 55percent water). Triethylamine (50 mL) was added and the mixture was hydrogenated under 500 psi/mole for 1.9 h. The reaction was filtered and the ethanol was washed with aqueous NHTo a solution of 3-amino-6-chloropyridazine (19.2 g, 148 mmol; CASNo. 5469-69-2) in EtOH (500 mL) was added 10percent Pd catalyst on 1940 carbon (unreduced, 55percent water). Triethylamine (50 mL) was added and the mixture was hydrogenated under 500 psi/mole for 1.9 h. The reaction was filtered and the ethanol was washed with aqueous NH

Molecular Weight:95.10
XLogP3:-1.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:95.048347172
Monoisotopic Mass:95.048347172
Topological Polar Surface Area:51.8
Heavy Atom Count:7
Complexity:54.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes