Trifluoroacetic acid → HCID 58709804, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (88.0 mg, 0.263 mmol), 3-chloro-5-(4-methylpiperazin-1-yl)-phenylamine (71.2 mg, 0.316 mmol), trifluoroacetic acid (243 μL, 3.16 mmol), and DMF (2 mL) was stirred in a sealed tube at 80° C. for 16 h. After cooling, N,N-diisopropylethylamine (550 μL, 3.16 mmol) was added, and the mixture turned into a dark clear solution. Into above solution was added tert-butyl isocyanate (36.0 μL, 0.316 mmol) and the solution was stirring at rt for 1 h. After that time, the mixture was concentrated in vacuo to obtain dark-brown oil that was submitted for MS-directed purification to obtain a light-brown oil. Further purification by HPLC gave the title compound as an off-white powder. 1H NMR (DMSO-d6, 400 MHz): δ=1.29 (s, 9H), 2.23 (s, 3H), 2.46 (t, 4H, J=4.6 Hz), 3.18 (t, 4H, J=4.8 Hz), 3.53 (t, 2H, J=5.4 Hz), 4.00 (brs, 2H), 5.79 (s, 1H), 6.43 (s, 1H), 6.63 (d, 1H, J=1.6 Hz), 6.78 (s 1H), 7.30 (s, 1H), 7.75 (d, 1H, J=1.6 Hz), 8.32 (s, 1H), 9.27 (s, 1H), 11.98 (s, 1H). MS (ES+): m/z 522.98/525.01(100/33) [MH+]. HPLC: tR=2.13 min (ZQ2000, polar—5 min).

Provenance & Evidence