Sodium hydride → HCID 51353708, compound

Participants

Reaction Steps

4-Methoxy-N-methylbenzenesulfonamide (228 mg, 1.13 mmol) was dissolved in DMSO (1.6 mL) and NaH (57.5 mg, 60% in mineral oil, 1.44 mmol) was added and the reaction was stirred under nitrogen at RT. After 1 hour, N-(6-(2-chloropyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide (82.3 mg, 0.270 mmol) was added, and the reaction flask was heated in a preheated oil bath (125° C.) and stirred under nitrogen overnight. The reaction was cooled to RT and filtered through a pad of Celite®(diatomaceous earth). Filtrate was concentrated and the crude material was purified on HPLC (10-95% MeCN/water with 0.1% TFA over 30 minutes) to provide N-(6-(2-(4-methoxy-N-methylphenylsulfonamido)pyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide. MS (ESI pos. ion) m/z: 470 (MH+). Calculated exact mass for C21H19N5O4S2: 469. 1H NMR (400 MHz, DMSO-d6): 12.52 (s, 1H), 8.64 (d, J=5.0 Hz, 1H), 8.56 (s, 1H), 8.14 (d, J=8.5 Hz, 1H), 7.99 (d, J=8.5 Hz, 2H), 7.84 (d, J=8.5 Hz, 1H), 7.72 (d, J=5.0 Hz, 1H), 7.10 (d, J=9.0 Hz, 2H), 3.82 (s, 3H), 3.69 (s, 3H), 2.23 (s, 3H).

Provenance & Evidence