Trifluoroacetic acid → HCID 136386510, compound

Participants

Reaction Steps

A mixture of tert-butyl 2-[[[phenyl(1H-pyrrolo[2,3-c]pyridin-3-yl)methylene]amino]oxy]ethylcarbamate (Example 111) (385.8 mg, 0.94 mmol), trifluoroacetic acid (4 mL) and methylene chloride (2 mL) was stirred at room temperature for 6 h. The solvent was removed in vacuo. The crude material was purified and free based using SCX-2 to give phenyl(1H-pyrrolo[2,3-c]pyridin-3-yl)methanone O-(2-aminoethyl)oxime (220 mg, 84%) as an off-white foam: 1H NMR (500 MHz, CD3OD) δ2.97-3.02 (2H, m), 3.20-3.31 (2H, m), 6.75-6.77 (0.6H, m), 7.19 (0.4H, m), 7.40-7.49 (5H, m), 7.91-7.92 (0.6H, m), 8.07-8.20 (1.5H, m), 8.70-8.72 (1H, m); ESI MS m/z 281 [C16H16N4O+H]+; HPLC (Method A) >99% (AUC), Isomeric ratio 58:42, tR=12.5 and 12.2 min.

Provenance & Evidence