Reaction Steps
To a suspension of benzothiazol-6-yl-[6-(1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amine tri-HCl (137 mg, 0.300 mmol), 3-pyridinylacetic acid-HCl (78.1 mg, 0.450 mmol), and EDC (115 mg, 0.600 mmol) in DMF (1 mL) was added N,N-diisopropylethylamine (0.261 mL, 1.50 mmol). The mixture became a clear solution after being stirred for a few minutes and was stirred overnight. The products, which precipitated from the solution during the reaction, were collected by filtration, washed with dichloromethane (2×1 mL), and dried in vacuo to afford the title compound as a white solid. 1H-NMR (DMSO-d6, 400 MHz): δ=2.73 (s, 2H), 2.89 (s, 2H), 3.78 (dt, J=4.0, 18.8 Hz, 2H), 3.86 (d, J=20 Hz, 2H), 4.19 (s, 1H), 4.33 (s, 1H), 6.45 (d, J=5.2 Hz, 1H), 6.84 (d, J=16.8 Hz, 1H), 7.33-7.36 (m, 1H), 7.65 (t, J=8.0 Hz, 1H), 7.87 (dt, J=2.0, 8.0 Hz, 1H), 7.95 (s, 1H), 8.04 (d, J=9.2 Hz, 1H), 8.34 (d, J=3.6 Hz, 1H), 8.44-8.48 (m, 1H), 8.92 (s, 1H), 9.24 (s, 1H), 9.62 (d, J=7.6 Hz, 1H). MS (ES+): m/z 467.94 [MH+]. HPLC: tR=1.98 min (ZQ2000, polar—5 min).
