Hydroxyamine hydrochloride → HCID 86645982, compound

Participants

Reaction Steps

A mixture of intermediate 13a (0.738 gr, 2.16 mmol), hydroxylamine hydrochloride (83 mg, 2.50 mmol) and sodium acetate (410 mg, 5 mmol) in EtOH (15 ml) was refluxed for 4 h. After cooling, the precipitate was collected by filtration and dried. The precipitated α-oximido-acetamidoxime sodium acetate derivative was refluxed with excess PCl5 in dry Et2O (15 ml) for 6 h. After cooling at room temperature the reaction was quenched with a buffered solution at pH 8.2 (10 ml) and the two phases separated. The aqueous layer was extracted with Et2O (2×10 ml) and the collected organic phases were dried over anhydrous Na2SO4 and evaporated under vacuum to give 4-[(1R)-1-{4-[(4-(trifluoromethyl)-1,3-thiazol-2-yl)amino]phenyl}ethyl]-1,2,5-oxadiazol-3-amine (0.57 g, 1.62 mmol) as a white solid (75%). 1H-NMR (DMSO-d6): δ 8.25 (bs, 1H, NH), 7.40 (d, 2H, J=7 Hz), 7.25 (d, 2H, J=7 Hz), 7.05 (s, 1H), 5.15 (bs, 2H, NH2), 3.90 (q, 1H, J=7 Hz), 1.75 (d, 3H, J=7 Hz).

Provenance & Evidence