Cyanogen Bromide → HCID 90047746, compound

Participants

Reaction Steps

To a suspension of 2-(6-phenylbenzo[d]thiazol-2-yl)acetohydrazide (105 mg, 0.33 mmol) (described in WO 2011/074560) in MeOH (4 mL) was added potassium bicarbonate (42 mg, 0.42 mmol) followed by cyanogen bromide (0.036 mL, 0.37 mmol) and the reaction mixture stirred for 3 h. The solvent was removed under reduced pressure and the residue purified on silica gel chromatography eluting with 0.5 to 8.5% MeOH/DCM to give Compound 89a (40 mg, 37% yield) as an orange solid. LCMS=1.75 min using analytical method (M), 309.0 (M+H). 1H NMR (400 MHz, CDCl3 containing CD3OD) δ 8.09 (d, J=1.5 Hz, 1H), 8.03 (d, J=8.5 Hz, 1H), 7.74 (dd, J=8.5, 1.8 Hz, 1H), 7.68-7.61 (m, 2H), 7.50-7.44 (m, 2H), 7.41-7.36 (m, 1H), 4.59 (s, 2H).

Provenance & Evidence