Ammonium formate → HCID 59591434, compound

Participants

Reaction Steps

A mixture of 3-[(5-chloro-1,3-benzothiazol-2-yl)methoxy]-2,6-difluoro-N′-hydroxybenzenecarboximidamide (156, mg, 0.42 mmol, 1 equiv.), 10% Pd/C (63 mg) and ammonium formate (133 mg, 2.1 mmol, 5 equiv.) in glacial acetic acid (2 ml) was stirred under reflux for 3 h. The mixture was filtered through a pad of celite, alkalised to pH 10 with 0.5N NaOH and extracted with EtOAc (3×15 ml). The combined organic extracts were dried (MgSO4) and evaporated to dryness under reduced pressure. The crude residue was dissolved in DMSO and precipitated by addition of H2O. The solid was filtered, washed with H2O and pentane, to give 49 mg (33% yield). Purity 62% by HPLC (Gemini C18, 50×4.6 mm): m/z 354 [M+H]+, Rt=3.09 min. HPLC-MS analysis suggested that there was also 6% un-reacted starting material and 21% of the title compound without the Cl atom.

Provenance & Evidence