HCID 57961833, compound → HCID 57962423, compound

Participants

Reaction Conditions

Reaction Steps

To a solution N-{3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}-3-nitrobenzenesulfonamide (0.5 g, 1.0 mmol) in water (0.9 mL), methanol (4.4 mL) and acetic acid (1.7 mL) was added iron (250 mg, 4.5 mmol) powder in one portion. The mixture was stirred at 0° C. for 1 h and then mixed with celite and filtered. The crude cake was washed with EtOAc. The brown filtrate was concentrated and mixed with EtOAc and NaHCO3/water. The aqueous phase was extracted once with EtOAc. The organic phases were combined and dried over Na2SO4. The volatiles were removed under vacuum to give the desired product (0.45 g, 100%). LCMS for C16H13Cl2N5O2S (M+H)+: m/z=410.0, 411.9. 1H NMR (400 MHz, DMSO-d6): δ 9.57 (s, 1H), 9.42 (s, 1H), 8.33 (s, 1H), 8.16 (s, 1H), 7.91 (s, 1H), 7.29 (dd, J=7.9, 7.6 Hz, 1H), 7.15 (d, J=7.9 Hz, 1H), 7.10-7.05 (m, 2H), 6.90 (dd, J=8.2, 0.9 Hz, 1H), 6.84-6.81 (m, 1H), 4.11 (s, 2H).

Provenance & Evidence