Benzenesulfonamide → HCID 57584955, compound

Participants

Reaction Steps

Benzenesulfonamide (150 mg, 0.954 mmol) was dissolved in DMSO (1.5 mL) and NaH (56.1 mg, 1.40 mmol, 60% in mineral oil) was added, and the reaction mixture was stirred at RT for 1 hour. N-(6-(2-Chloropyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide (50.2 mg, 0.165 mmol) was added, and the reaction flask was placed in a preheated oil bath (125° C.) and stirred under nitrogen. The reaction was stirred for 21 hours, and then cooled to RT and quenched with MeOH. The suspension was filtered through a pad of Celite® (diatomaceous earth), which was washed with DCM and MeOH, and the filtrate was concentrated, and purified on an HPLC system (10-95% MeCN/water with 0.1% TFA over 30 minutes) to provide N-(6-(2-(phenylsulfonamido)pyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide (29 mg, 41%). MS (ESI pos. ion) m/z: 426 (MH+). Calculated exact mass for C19H5N5O3S2: 425. 1H NMR (400 MHz, DMSO-d6): 12.53 (s, 1H), 8.54-8.56 (m, 2H), 8.09 (d, J=9.0 Hz, 1H), 8.05 (d, J=7.5 Hz, 2H), 7.83 (d, J=8.5 Hz, 1H), 7.58-7.63 (m, 4H), 2.24 (s, 3H).

Provenance & Evidence