Pyridine → HCID 67156780, compound

Participants

Reaction Steps

3,4-Dichloroaniline (0.49 mmol), was dissolved in acetonitrile (1 mL) and pyridine (0.440 mL, 4.03 mmol) was added to a solution of 4-chlorothieno[3,2-c]pyridine-2-sulfonyl chloride (0.445 mmol) dissolved in acetonitrile (1 mL). The reaction was shaken for 1 h, controlled with HPLC and the solvent was removed. The crude product was used in the next step without further purification. To the reaction mixture from the previous step, dissolved in DMSO (1 mL), piperazine (15 equiv.) and K2CO3 (1 equiv.) was added. The reaction was stirred at 100° C. for 24 and than concentrated. The product was purified by LC-MS and gave 5.8 mg (2.6%) of the title product. 1H NMR (270 MHz, CH3OH-d4) δ ppm 8.07-8.05 (m, 2H) 7.73 (d, J=6.60 Hz, 1H) 7.46-7.41 (m, 2H) 7.16 (dd, J=8.71, 2.38 Hz, 1H) 3.94-3.90 (m, 4H) 3.92 (m, 4H) 3.53-3.50 (m, 4H); LC-MS 443 (M−H)+; Purity (HPLC) 95%.

Provenance & Evidence