Sodium Thiosulfate → HCID 69794758, compound

Participants

Reaction Steps

To N-methyl-4-[3-(methylthio)-4-({[(2,2,4,4-tetrafluoro-4H-1,3-benzodioxin-6-yl)-amino]carbonyl}amino)phenoxy]pyridine-2-carboxamide (150 mg, 0.28 mmol) in anhydrous 1:1 v/v DCM/THF (3.0 mL) at 0° C. was added mCPBA (162.7 mg, 0.61 mmol, 2.2 eq, and the reaction mixture was stirred at RT for 17 h. The reaction mixture was poured into aqueous saturated sodium thiosulfate solution and extracted with EtOAc (3×100 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and evaporated under reduced pressure to give 73.3 mg (46.1%) of the title compound as a white solid. 1H-NMR (DMSO-d6) δ 10.31 (s, 1H), 8.81 (q, J=5.4 Hz, 1H), 8.71 (s, 1H), 8.55 (d, J=5.7 Hz, 1H), 8.23 (d, J=9.0 Hz, 1H), 8.15 (d, J=2.4 Hz, 1H), 7.70 to 7.59 (m, 3H), 7.47 (s, 1H), 7.45 (d, J=6.9 Hz, 1H), 7.21 (dd, J=5.4, 2.4 Hz, 1H), 3.37 (s, 3H), 2.79 (d, J=5.1 Hz, 3H); MS LC-MS (M+H)+=571.1, RT=3.81 min; m.p. 222-223.5° C.

Provenance & Evidence