Chlorosulfamic acid → HCID 58346566, compound

Participants

Reaction Steps

To 5 mL DMA cooled to 5° C. was added 2-[6-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-4,5-dihydro-2H-pyrimido[5′,4′:4,5]thieno[2,3-e]indazol-2-yl]ethanol (100 mg, 0.19 mmol) followed by chlorosulfonyl amine (221 mg, 1.9 mmol). The mixture was stirred with warming to rt over a 2 h period, after which time stirring was halted. The entire mixture was poured onto cold brine (10 mL), upon which precipitation of a solid occurs. The mixture was filtered, and the filtrate extracted with CH2Cl2 (3×10 mL). The combined organic layers were dried over MgSO4, filtered, and the solvent removed under reduced pressure. The crude residue was purified by reverse phase HPLC. The product fractions were combined and diluted with CH2Cl2 (50 mL), and neutralized with NaHCO3 (50 mL). The organic layer was dried over MgSO4, filtered, and the solvent removed under reduced pressure to afford the final pure product (30 mg, 26%) as a white solid. 1H-NMR (DMSO-d6) δ 8.40 (s, 1H), 8.33 (s, 1H), 7.98 (s, 1H), 7.75 (s, 1H), 7.59 (s, 2H), 7.51 (dd, 1H), 7.40 (dd, 1H), 6.91-7.11 (m, 4H), 5.21 (s, 2H), 4.38 (br s, 4H), 3.32 (t, 2H), 2.90 (t, 2H); LCMS RT=3.45 min; [M+H]+=601.2.

Provenance & Evidence