Hydrochloric Acid → HCID 136386516, compound

Participants

Reaction Steps

(3,4-Dichlorophenyl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone (Example 127) (92 mg, 0.32 mmol) and tert-butyl[2-(aminooxy)ethyl]carbamate (58 mg, 0.33 mmol) were combined in ethanol (5 mL). The pH was adjusted to ca. 4 using 1 M ethereal hydrogen chloride and the react ion mixture was refluxed for 14 h. The solvent was removed under vacuum. The residue was dissolved in ethyl acetate, washed with saturated sodium bicarbonate solution and then brine, dried over sodium sulfate, and concentrated to a solid. Purification by Biotage chromatography (silica gel, 97:3 CH2Cl2:CH3OH) produced tert-butyl 2-[[[(3,4-dichlorophenyl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methylene]amino]oxy]ethylcarbamate (74 mg, 51%) as a yellow foam: 1H NMR (300 MHz CD3OD) δ 1.39 (9H, s), 3.50-3.54 (2H, m), 4.26-4.39 (2H, m), 6.35 (0.35H, s), 6.62 (0.65H, s), 7.38-7.77 (4H, m), 8.04-8.11 (1H, m), 8.72 (0.35H, s), 8.93 (0.65H, s); ESI MS m/z 449 [C21H22Cl2N4O3+H]+.

Provenance & Evidence