Trifluoroacetic acid → HCID 58709949, 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 (54.5 mg, 0.163 mmol), 5-amino-1-phenyl-1H-pyridin-2-one hydrochloride (43.5 mg, 0.195 mmol), dimethyl sulfoxide (3 mL) and trifluoroacetic acid (125 μl, 1.63 mmol) in a sealed tube was heated at 100° C. overnight. The mixture was concentrated in vacuo and was charged with N,N-dimethylformamide (2 mL), triethylamine (272 μL, 1.95 mmol) and tert-butyl isocyanate (20.4 μl, 0.179 mmol). The above mixture was stirred at rt for 1.5 h, concentrated in vacuo, and partitioned between water/EtOAc (10 mL/15 mL). The aqueous phase was extracted with EtOAc (2×15 mL), and the combined organic phase was washed with brine (10 mL), concentrated in vacuo, and dissolved in DMSO/MeOH for submission for MS-directed purification, which gave the title compound as beige solid. 1H NMR (CD3OD, 400 MHz): δ=1.46 (s, 9H), 2.67 (brs, 2H), 3.69-3.72 (m, 2H), 4.16(brs, 2H), 6.41 (brs, 1H), 6.72 (s, 1H), 6.79 (d, 1H, J=9.6 Hz), 7.56-7.68 (m, 5H), 7.95 (dd, 1H, J=2.8 & 9.6 Hz), 8.27 (s, 1H), 8.39 (d, 1H, J=2.4 Hz), 8.64 (s, 1H). MS (ES+): m/z 484.09 (100) [MH+]. HPLC: tR=2.44 min (ZQ2000polar—5 min).

Provenance & Evidence