3-PYRIDAZINECARBOXYLIC ACID, 6-AMINO-, ETHYL ESTER

2-Bromo-1, 1-diethoxy-ethane (16.55 g, 12.63 mL, 84 mmol) was dissolved in hydrogen bromide (3.52 mL of 48% w/v, 20.88 mmol) and stirred at 120 C for 30 minutes. The reaction mixture was allowed to cool to ambient temperature and EtOH (100 mL) was added, followed by NaHCO3 (3.196 g, 38.04 mmol) and Slowly adding sodium (7.2 g) in ethanol (800 mL), and stirred for 2 hours at room temperature.After confirming that all the sodium had dissolved, the mixture was further stirred at room temperature for 1 hour added the commercially available methyl 6-amino-pyridazine-3-carboxylate (40.0g).Hydrogen chloride to the reaction solution (4.0mol / L ethyl acetate solution, about 80mL) was adjusted to dropped about pH5 a.The resulting reaction solution was concentrated to dryness, filtered after suspending further washed with distilled water, by air drying, to give the title compound 39.9g (99%).General procedure: A round bottom flask equipped with reflux condenser and magnetic stirring bar was charged with substituted heteroaryl chloride (5 mmol), sodium azide (10 mmol), triphenylphosphine (10 mmol) and DMSO (40 ml). The reaction mixture was stirred at 120 C. Reaction progress was monitored by TLC. In 3-5 hours starting material was disappeared and new product was confirmed by TLC. 1N HCl (8 mL) was added to the reaction mixture and continued to stir at 120 C for additional 1-2 hour. Reaction mixture was cooled to room temperature and diluted with 1N HCl (8 mL). The resulting mixture was poured into distilled water (100 mL) and aqueous layer was washed with EtOAc (2 X 50 mL) to remove triphenylphosphine oxide. Aqueous layer was slowly neutralized with saturated aqueous NaHCO3 solution and extracted with EtOAc (2 X 50 mL). The combined organic layers were washed with water (40 mL), brine(40 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to afford substituted heteroaryl amine with high purity without column purification (purity was achieved in some products by washing solid compound with n-Pantane).A mixture of crude tert-butyl (1 -{4-[bromo(phenyl)acetyl]phenyl}cyclobutyl)carbamate that was prepared in a manner analgous to that described for Intermediate Example lnt-1 -A (3.3 g, -80% purity, 5.79 mmol),

Molecular Weight:167.17
XLogP3:-1.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:3
Exact Mass:167.069476538
Monoisotopic Mass:167.069476538
Topological Polar Surface Area:78.1
Heavy Atom Count:12
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes