ETHYL 3,6-DICHLOROPYRIDAZINE-4-CARBOXYLATE

To a mixture of 3, 6-dichloropyridazine-4-carboxylic acid (15.0 g, 78 mmol) in THF (150 mL) was added ethanol (18.15 mL, 311 mmol) and DMAP (0.950 g, 7.77 mmol). EDC (16.39 g, 85 mmol) was then added in portions over 1 min. The reaction was mildly exothermic. The reaction was stirred at room temperature for 16 h. The reaction mixture was transferred to a separatory funnel containing saturated aqueous NaHCCb solution (150 mL). The aqueous layer was extracted with ether (3 x 250 mL). The combined organic layers were washed with brine (100 mL), dried over MgSCn, filtered, and concentrated. The residue was purified by column chromatography on silica gel (20percent→ 40percent ethyl acetate in hexanes; 300 g column) to afford ethyl 3, 6-dichloropyridazine-4- carboxylate (13.2 g, 59.7 mmol, 77percent yield) as a colorless oil: NMR (400MHz, CDCh) δ 7.88 (s, 1H), 4.50 (q, J=7.0 Hz, 2H), 1.46 (t, J=7.2 Hz, 3H); LCMS (ESI) m/e 221.1 [(M+H)[00148] To a solution of 3, 6-dichloropyridazine-4-carboxylic acid (5 g, 25.9 mmol), EtOH (4.77 g, 104 mmol), and DMAP (317 mg, 2.59 mmol) in THF (30 mL) was added EDCI (5.46 g, 28.5 mmol). The reaction mixture was stirred for 50 min.After this time, the solvent was removed in vacuo and EtOAc (200 mL) was added.Upon completion of addition, the resulting mixture was washed with 100 mL each of water, saturated aqueous NaHCψ3, and brine, dried over MgSOEthyl 3, 6-dichloropyridazine-4-carboxylate A mixture of

Molecular Weight:221.04
XLogP3:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:219.9806328
Monoisotopic Mass:219.9806328
Topological Polar Surface Area:52.1
Heavy Atom Count:13
Complexity:191
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes