6-Chloro-3-pyridazinecarboxylic acid

6-Chloropyridazine-3-carboxylic acid is Brown green powder

Procedure for synthesis of 6-chloropyridazine-3-carboxylic acid (Step-1) To a mixture of ethyl 6-chloropyridazine-3-carboxylate (commercially available) (1.00 g, 5.36 mmol) in THF (10 mL) was added LiOH (0.655 g, 26.8 mmol, 5 equiv.) in water (10 mL). The resulting reaction mixture was stirred at ambient temperature for 45mins. The reaction mixture was poured into 2M hydrochloric acid and extracted with DCM. The organics were combined and evaporated to give product as a white solid (770 mg, 91 percent). LC-MS: (positive ES MH+ 159/161 ).A. A. PREPARATION 2 Potassium dichromate (3.3 g, 11.2 mmol) was added in portions to a solution of 3-Chloro-6-methyl-pyridazine (1.2 g, 9.3 mmol) in [H2SO4] (10 ml). After addition the mixture is stirred at 50 [°C] on. The reaction was pored on ice and the mixture was extracted three times with diethyl ether. The combined organic phases were dried and concentrated to give the title compound (840 mg, 57percent). [LC-MS] [(M++1)] : 159 and 161 (3: 1).To a stirred solution of 3-chloro-6-methylpyridazine (5.0 g, 39.0 mmol) in concentrated H3-Chloro-6-methylpyridazine (3.00 g, 23.3 mmol) was dissolved in concentrated sulfuric acid (23 mL), and potassium dichromate (8.24 g, 28.0 mmol) was added little by little under ice cooling. The mixture was stirred at room temperature for 1.5 hours, and the mixture was further stirred at 50°C for 60 hours. The reaction mixture was slowly poured into ice water, and the mixture was extracted with diethyl ether (x 3). The organic layer was washed with saturated sodium chloride solution and dried with anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure to give the title compound (1.27 g; yield, 34percent) as a white solid. 6-Chloro-pyridazine-3-carboxylic Acid β-Chloro-pyridazine-S-carboxylic acidA mixture of 3-chloro-6-methyl-pyridazine (10.0 g, 77.8 mmol) and KTo an aqueous solution (2 ml) of disodium hydrogen phosphate dodecahydrate (50 mg), were added acetnitrile (3 ml), 6-chloro-3-pyridazinecarboxyaldehyde (0.10 g, 0.70 mmol), 31percent aqueous hydrogen peroxide (0.12 g, 1.1 mmol) and sodium chlorite (0.10 g, 1.1 mmol), and stirred for 3 hours. A suspension of (1) (2.0g, 12.7mmol) and 4-(dimethylamino)pyridine (776mg, 6.3mmol) in THF (50ml_) was treated with di-fe/f-butyl dicarbonate (3.6g, 16.5mmol). It was heated up to 50C for 1 h, then stirred at rt overnight. The reaction mixture was concentrated in vacuo, re-dissolved in EtOAc (20ml_), poured into HCI solution (1 M, 20ml_) and extracted with EtOAc (2 x 20ml_). The combined organics were washed with NaHC03 solution (50ml_) and brine (50ml_), dried over MgS04, filtered and concentrated in vacuo. Purification by silica gel column chromatography with hexane/EtOAc (1 :0-3: 1 ) yielded (2) as a white solid (2.2g, 81 %). (0878) LCMS (ES): Found 237.0 [M+Naf. (0879) 1H NMR (300 MHz, Chloroform-cf), d: 8.08 (d, J= 8.7 Hz, 1 H), 7.63 (d, J=8.9 Hz, 1 H), 1.67 (s, 9H).

A pyradazine derivative used in the preparation of stearoyl-CoA desaturase inhibitors.

Molecular Weight:158.54
XLogP3:0.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:157.9883050
Monoisotopic Mass:157.9883050
Topological Polar Surface Area:63.1
Heavy Atom Count:10
Complexity:142
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes