2-Aminopyridine → HCID 131727228, compound

Participants

Reaction Steps

A solution of 2-aminopyridine (22.6 mg, 0.24 mmol) and diimidazol-1-ylmethanone (CDI, 39 mg, 0.24 mmol) in DMF (0.75 mL) was stirred at 50° C. for 1 h. After cooling to rt, i-Pr2NEt (0.14 mL, 0.8 mmol) was added, followed by (1H-indazol-5-yl)-[6-(1,2,3,6-tetrahydropyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amine tri-HCl (88.1 mg, 0.2 mmol). The mixture was stirred at rt for 2 h and 50° C. for 3 h. The resulting mixture was filtered and submitted to mass-directed HPLC purification to yield the title compound. 1H-NMR(CD3OD, 400 MHz): δ=2.66 (m, 2H), 3.88 (t, J=6.0 Hz, 2H), 4.37 (m, 2H), 6.45 (s, 1H), 6.71 (s, br, 1H), 7.38 (t, J=6.0 Hz, 1H), 7.48 (dd, J=2.0, 9.2 Hz, 1H), 7.66 (d, J=8.8 Hz, 1H), 7.76 (d, J=8.8 Hz, 1H), 7.98 (d, J=1.2 Hz, 1H), 8.16 (d, J=12.4 Hz, 1H), 8.22 (dt, J=1.6, 8.8 Hz, 1H). 8.29 (d, J=6.0 Hz, 1H). MS (ES+): m/z 451.95 [MH+]. HPLC: tR=1.77 min (ZQ2000, polar—5 min).

Provenance & Evidence