Tert-Butylamine → HCID 57585160, compound

Participants

Reaction Steps

A microwave vial equipped with a magnetic stir bar was charged with 2-methylpropan-2-amine (0.100 g, 2 mmol) in DMF (3 ml). Then sodium hydride (0.047 g, 2.0 mmol) was added into the mixture and allowed to stir an additional 15 minutes. Then N-(6-(6-chloropyrazin-2-yl)benzo[d]thiazol-2-yl)acetamide (0.100 g, 0.30 mmol), palladium(II) acetate (0.007 g, 0.03 mmol) and Xantphos (0.010 g) was added to the mixture. The vial was capped and placed into a CEM Microwave for 10 minutes at 100° C., while 100 watts of energy was supplied via Powermax® (Simultaneous heating while cooling technology). The progress of the reaction was monitored by LC/MS, which showed desired product in the mixture. The mixture was placed into a round-bottom flask, then diluted with ethyl acetate (20 ml) and stirred 20 minutes. The precipitate was collected by filtration and then purified by reverse-phase HPLC. This gave N-(6-(6-(tert-butylamino)pyrazin-2-yl)benzo[d]thiazol-2-yl)acetamide (0.005 g, 4% yield) as a tan crystalline solid. MS (ESI pos. ion) m/z: 342 (MH+). Calc'd exact mass for C17H19N5OS: 341. 1H NMR 400 MHz, DMSO-d6): 1.49 (s, 9H), 2.09 (s, 3H), 6.80 (s, 1H), 7.62 (d, J=8.03 Hz, 1H), 7.82 (s, 1H), 7.98 (d, J=8.03 Hz, 1H), 8.24 (s, 1H), 8.43 (s, 1H).

Provenance & Evidence