Hydrochloric Acid → Octanedioic acid hydroxyamide [4-(2-amino-phenyl)-thiazol-2-yl]-amide

Participants

Reaction Conditions

Reaction Steps

To a mixture of compound 15 (0.040 g, 0.083 mmol) in methanol (2 ml) was added 1 ml of concentrated HCl. The suspension was cooled to 0° C. Then SnCl2 (0.094 g, 0.49 mmol) was added and the reaction mixture was stirred overnight at room temperature. The mixture was then diluted with 5 ml of water, adjusted to pH 10 with 5N NaOH and extracted with ethyl acetate (10 mL×3). The combined organic layers were washed with water, dried over K2CO3 and concentrated in vacuo. The crude product was purified by reverse phase HPLC to afford Octanedioic acid hydroxyamide [4-(2-amino-phenyl)-thiazol-2-yl]-amide 16 (0.016 g, 53% yield). NMR (400 MHz, DMSO-d6 cont 5% TFA) δ (ppm) 12.13 (1H, s), 7.56 (1H, d, J=7.0 Hz), 7.40 (1H, s), 7.09 (1H, t, J=7.0 Hz), 6.83 (1H, d, J=7.0 Hz), 6.72 (1H, m), 3.75-3.39 (4H, brs), 2.44 (2H, t, J=7.3 Hz), 2.29 (2H, t, J=7.3), 1.61 (2H, m), 1.51 (2H, m), 1.30 (4H, m).

Provenance & Evidence