Hydrochloric Acid → HCID 58709974, compound

Participants

Reaction Conditions

Reaction Steps

3-[3-(2-Dimethylaminoethyl)-3H-imidazol-4-yl]phenylamine (110 mg, 0.478 mmol) was added to a solution of tert-butyl 4-(chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylate (133 mg, 0.398 mmol) in 1-butanol (2.0 mL). The reaction was stirred at 120° C. for 48 h. 0.8 mL of 1 N HCl in ether was then added and the mixture was stirred further at 120° C. for 15 h. LC-MS showed the displacement reaction was complete and the BOC group in the desired product was completely removed. Di-tert-butyldicarbonate (347 mg, 1.59 mmol) and N,N-diisopropylethylamine (0.347 mL, 1.99 mmol) were added, and the resulting mixture was stirred at rt for 30 min. DMF (z1.5 mL) was added and the mixture was filtered. The filtrate was purified by HPLC purification to give the title compound. 1H-NMR (CD3OD, 400 MHz): δ=1.50 (s, 9H), 2.52 (s, 6H), 2.58 (m, 2H), 3.04 (t, J=6.8 Hz, 2H), 3.67 (m, 2H), 4.13 (m, 2H), 4.53 (t, J=6.8 Hz, 2H), 6.30 (s, br, 1H), 6.72 (s, 1H), 7.18 (s, 1H), 7.19 (d, J=7.6 Hz, 1H), 7.48-7.52 (m, 1H), 7.72 (dd, J=2.4, 8.0 Hz, 1H), 8.06 (s, 1H), 8.12 (m, 1H), 8.26 (s, 1H). MS (ES+): m/z 529 [MH+]. HPLC: tR=2.00 min (ZQ2000, polar—5 min).

Provenance & Evidence