2-Pyridinesulfonamide(6CI,7CI,9CI)

To 1000 mL of a round-bottomed flask were added CH2Cl2 (200 mL) and 1Maqueous HCl (200 mL, 200 mmol, 5.0 equiv.) and the suspension was cooled to -5 to -10 °C (bath temp.) using ice-salt bath. To the well-stirred suspension was added 2-mercaptopyridine (4.45 g, 40 mmol) and the resulting yellow mixture was stirred for10 min, then NaOCl (6percent solution, 208 mL, 132 mmol, 3.3 equiv.) was addeddropwise over 5 min. After the addition, the mixture was stirred for 10 min at thesame temperature and decanted to a separatory funnel. The separated organic layerwas immediately added dropwise to a pre-cooled, stirred mixture of a saturated NH3solution in MeOH (80 mL) and CH2Cl2 (80 mL) at 0 °C. The aqueous layer in the separatory funnel was washed twice with CH2Cl2 and the organic layers were addeddropwise to the NH3 solution. The resulting white suspension was warmed to roomtemperature and stirred for 2 h. The solvent was then evaporated to give a white solid, which was dissolved in hot AcOEt (250 mL × 2) and filtered through a filter paper toremove NH4Cl. The filtrate was evaporated to give the crude product, which wasrecrystallized from AcOEt with hexane to give pure 2-pyridinesulfonamide (4.15 g, 70percent yield). 1H NMR (500 MHz, DMSO-d6) δ 8.72 (d, J = 5.4 Hz, 1H), 8.07 (td, J =7.7, 1.7 Hz, 1H), 7.94 (d, J = 7.9 Hz, 1H), 7.64 (ddd, J = 7.6, 4.7, 1.1 Hz, 1H), 7.47 (s, 2H). 13C NMR (125 MHz, DMSO-d6) δ 159.79, 149.55, 138.45, 126.54, 120.36.A 1.0 M solution of HCI (45 mL) and DCM (45 mL) was cooled to -10 °C and pyridine-2-thiol (1 .0 g, 9.0 mmol) added. After 10 min, NaOCI (6percent solution, 47 mL, 3.3 eq.) was added drop-wise over 5 min and stirring continued at -10 °C for 10 min. The organic phase was separated, dried using Nab. 2-Pyridinesulfonamide. The product of Example 9a was dissolved in a mixture of CH2Cl2/Et2O(1:2) and cooled to -30C. Gaseous NH3 was bubbled into the solution for 10 min. The reaction was stirred overnight and allowed to warm to room temperature. The reaction mixture was filtered; and the precipitate was suspended in EtOAc/EtOH (3:1) and filtered. The combined filtrates were concentrated to give the product as a white solid (308 mg); TLC, Rf=0.44, MeOH:CHCl3 (5:95).

Molecular Weight:158.18
XLogP3:-0.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:158.01499861
Monoisotopic Mass:158.01499861
Topological Polar Surface Area:81.4
Heavy Atom Count:10
Complexity:194
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes