Hydrochloric Acid → 2-[[[phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methylene]amino]oxy]acetamide

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Reaction Steps

1 N HCl (0.67 mL, 0.67 mmol) was added to a solution of 2-(aminooxy)acetamide (Reference Example 18) (90.5 mg, 1.04 mmol) in EtOH (6.7 mL) followed by addition of phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone (Example 35) (150 mg, 0.67 mmol). The reaction mixture was refluxed overnight. The reaction mixture was cooled to room temperature and the solvent was removed in vacuo. The residue was free based using an SCX-2 and purified by Biotage chromatography to isolate 2-[[[phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methylene]amino]oxy]acetamide (72.9 mg, 37%) as a white solid (single isomer, geometry of the oxime double bond undefined): Rf 0.13 (90:10 methylene chloride/methanol); 1H NMR (500 MHz, DMSO-d6) δ4.65 (2H, s), 6.65 (1H, s), 7.41-7.58 (8H, m), 8.14-8.15 (1H, d, J=5.5 Hz), 8.89 (1H, s), 12.01 (1H, br s); ESI MS m/z 295 [C16H14N4O2+H]+; HPLC (Method A) 98.9% (AUC), tR=14.8 min.

Provenance & Evidence