Pyridine → HCID 10455065, compound

Participants

Reaction Steps

To a solution of 4-chloro-thieno[3,2-c]pyridine-2-sulfonyl chloride (0.640 g, 2.39 mmol) in DCM (20 mL) was added pyridine (1.9 mL, 23.9 mmol) followed by p-tolylamine (0.307 g, 2.86 mmol). The reaction mixture was stirred at room temperature for 16 hours. The mixture was concentrated and re-dissolved in DMSO (10 mL), piperazine-1-carboxylic acid tert-butyl ester (1.34 g, 7.17 mmol) and K2CO3 (0.989 g, 7.17 mmol) were added. The mixture was stirred at 100° C. for 16 hours and then concentrated. The crude reaction mixture was dissolved in EtOAc (100 mL) and washed with brine (2×50 mL). The organic phase was dried (Na2SO4) and concentrated. The crude intermediate was purified by column chromatography on silica using EtOAc/n-pentane (1:1) as eluent. The intermediate was dissolved in EtOAc/MeOH and diethyl ether saturated with HCl (g) was added. The mixture was stirred at room temperature for 16 hours. The precipitate was collected by filtration and washed with diethyl ether/n-pentane to give 0.475 g of the crude product. Purification by preparative reversed phase HPLC gave 0.133 g of the pure product: 1H NMR (DMSO-d6, 25° C., 270.17 MHz) δ 10.61 (br s, 1H), 9.23 (br s, 2H), 8.13 (d, J=5.80 Hz, 1H), 7.91 (s, 1H); 7.67 (d, J=5.80 Hz, 1H), 7.09-7.07 (m, 4H), 3.68-3.59 (m, 4H), 3.33-3.22 (m, 4H), 2.20 (s, 3H); m/z (posESI) 399 (M+H).

Provenance & Evidence