Benzenesulfonamide, N,4-dimethyl- → HCID 51354023, compound

Participants

Reaction Steps

A microwave vial equipped with a stir bar was charged with N-methyl-p-toluenesulfonamide (0.23 g, 1.2 mmol) in DMF (3 mL). NaH (0.12 g, 4.9 mmol) was added to the mixture and allowed to stir for 30 minutes. Then, palladium (II) acetate (0.011 g, 0.049 mmol), N-(6-(2-chloropyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide (0.150 g, 0.492 mmol), and Xantphos (0.010 g) were added to the mixture. The vial was capped and placed into a microwave for 10 minutes at 100° C. The mixture was then added to a RBF, diluted with water (150 mL), and allowed to stir overnight. The resulting precipitate was collected by filtration and washed with hexane and 1:1 hexanes/ethyl ether to provide N-(6-(2-(N,4-dimethylphenylsulfonamido)pyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide as a tan solid. MS (ESI pos. ion) m/z: 454 (MH+). Calculated exact mass for C21H19N5O3S2: 453. 1H NMR (400 MHz, DMSO-d6): 12.52 (s, 1H), 8.64 (s, 1H), 8.48 (s, 1H), 8.10 (d, J=5.0 Hz, 1H), 7.93 (s, 2H), 7.83 (s, 1H), 7.71 (s, 1H), 7.40 (s, 2H), 3.70 (s, 3H), 2.37 (s, 3H), 2.24 (s, 3H).

Provenance & Evidence