2-Aminopyridine → HCID 44234336, compound

Participants

Reaction Steps

7,8-Dichloro-5-oxo-2,3,4,5-tetrahydro-benzo[b]oxepine-4-carboxylic acid methyl ester (0.2 mmol) and 2-aminopyridin (0.2 mmol) were dissolved in 1 ml xylene. Reaction was performed by microwave irradiation for one hour at 150° C. The solution obtained from this reaction was cooled to room temperature and extracted by 2 mol/l hydrochloric acid and ethyl acetate. The ethyl acetate extract was dried over sodiumsulfate and the solvent removed in vacuo. The remaining residue was purified via HPLC (Chromolith prep. RP18, Solvent A water:acetonitrile 90:10+0.1% formic acid, solvent B: water:acetonitrile 10:90+0.1% formic acid, flow: t=0 min 25 ml/min, t=1 min 50 ml/min, gradient: t=0 min 10% B, t=1 min 10% B, t=2 min 10% B, t=2.2 min 20% B, t=7.5 min 50% B, t=7.6 min 100% B, t=8.5 min 100% B). After evaporation of the solvent in vacuo 7,8-Dichloro-5-oxo-2,3,4,5-tetrahydro-benzo[b]oxepine-4-carboxylic acid pyridine-2-ylamide was obtained as a white powder in a yield of 14%. LC-MS: 1.9 min, 351.0 (MH+), 1H-NMR: (DMSO-d6, 500 MHz): □ [ppm]: 10.543 (s, 1H), 8.304 (s, 1H), 8.135 (d, 1H, J=8.1 Hz), 7.809 (t, 1H, J=7.6 Hz), 7.758 (s, 1H), 7.524 (s, 1H), 7.114 (s, 1H), 4.652 (m, 1H, J=2.8 Hz), 4.360 (t, 1H, J=8.9 Hz), 4.042 (m, 1H, J=4.9 Hz), 2.512 (m, 2H, J=1.8 Hz)

Provenance & Evidence