Thionyl Chloride → HCID 86626539, compound

Participants

Reaction Steps

2-(6-Methoxypyridin-3-yl)-1,3-benzothiazole-6-carboxylic acid (40 mg, 0.14 mmol) was mixed with thionyl chloride (1 mL) and stirred at r.t. for 3 h, then heated to 50° C. for 1 h. The solvent was evaporated in vacuo to give the intermediate, 2-(6-methoxypyridin-3-yl)-1,3-benzothiazole-6-carbonyl chloride as a crude product. This acid chloride was dissolved in DCM (3 mL) and added to pyrrolidine (0.5 mL) in CH2Cl2 (1.5 mL). The reaction was stirred at r.t. for 1 h. Water was added and the reaction mixture was extracted, twice, with DCM, dried (MgSO4), filtered and the solvent was evaporated. The solid was dried (in vacuo over P2O5) to give the title compound (45 mg) as an off-white solid. 1H NMR δ 8.92 (d, 1H) 8.39 (dd, 1H) 8.35 (s, 1H) 8.07 (d, 1H) 7.67 (d, 1H) 7.04 (d, 1H) 3.97 (s, 3H) 3.51 (t, 2H) 3.45 (t, 2H) 1.78-1.95 (m, 4H); MS m/z (M+H) 340.

Provenance & Evidence