Thionyl Chloride → HCID 86626538, compound

Participants

Reaction Conditions

Reaction Steps

2-[6-(4-Methylpiperazin-1-yl)pyridin-3-yl]-1,3-benzothiazole-6-carboxylic acid hydrochloride acid (46 mg, 0.12 mmol) was added to thionyl chloride (3 mL), followed by 3 drops DMF, before heating at 70° C. o.n. The solvent was thereafter evaporated in vacuo and once with toluene to give crude 2-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]-1,3-benzothiazole-6-carbonyl chloride. Ammonium hydroxide (conc., 3 mL) was added dropwise to this crude product and the mixture was thereafter stirred for 1 h at r.t. The r.m. was extracted twice with DCM, dried (Na2SO4), and evaporated in vacuo. The obtained residue was purified by prep. HPLC to give the title compound (7 mg) as a light yellow solid. 1H NMR δ 8.81 (d, 1H) 8.58 (s, 1H) 8.16 (dd, 1H) 8.07 (br. s., 1H) 7.99 (s, 2H) 7.45 (br. s., 1H) 7.00 (d, 1H) 3.61-3.71 (m, 4H) 2.37-2.46 (m, 4H) 2.23 (s, 3H) 1.89 (s, 3H); MS m/z (M+H) 354.

Provenance & Evidence