5-Amino-1-(4-(methylsulfonyl)phenyl)-1H-pyrazole-4-carbonitrile

A round-bottomed flask (100 mL), equipped with a reflux condenser and N2 inlet septum, was charged with 4- (methylsulfonyl) phenylhydrazine hydrochloride (2 g, 9 mmol), and sodium methoxide (0. 49 g, 9 mmol). Methanol (20 mL) was added under a stream of nitrogen at room temperature. The reaction mixture was stirred for 15-20 minutes until the purple color disappeared and a white precipitate was formed. This was followed by the addition of ethoxymethylenemalononitrile (1.1 g, 9 mmol) and stirring at room temperature for an additional 10 mins, subsequently the reaction mixture was brought to reflux for 150 mins. The cooled reaction mixture was filtered and concentrated under reduced pressure to afford the crude product. The solid residue was dissolved in ETOAC/H20. The EtOAc layer was collected, washed with saturated aqueous NACI, dried OVER NAS04 AND concentrated to give second portion of the crude product. The crude product was purified by flash chromatography (10 percent CH3OH/CH2CI2) and recrystallized from methanol to give a yellow crystalline product (625 mg, 26 percent). 'H NMR (DMSO-D6, 400 MHz) No. 3. 27 (s, 3H), 6. 98 (s, 2H), 7. 81 (d, 2H), 7. 88 (s, 1H), 8. 06 (s, 2H). LCMS : calculated for CIIHIONAO2S 262. 05, observed 262. 9 (MH+)

Molecular Weight:262.29
XLogP3:1.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:262.05244675
Monoisotopic Mass:262.05244675
Topological Polar Surface Area:110
Heavy Atom Count:18
Complexity:441
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes