Benzenesulfonyl chloride → HCID 70135804, compound

Participants

Reaction Steps

To a stirred solution of 2-[(piperidin-3-yl)-methylamino]-4-[benzimidazol-1-yl]pyrimidine (20 mg, 0.065 mmol, 1 eq) in THF (1 mL) at 0° C. was added diisopropylethylamine (0.023 mL, 0.13 mmol, 2 eq) followed by addition of benzenesulfonylchloride (0.009 mL, 0.071 mmol, 1.1 eq) via syringe. Removed the cooling bath and let stir for 1 h. Quenched the reaction with saturated aqueous NaHCO3 and extracted 3× with CH2Cl2. Combined the organic extracts, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by preparative thin layer chromatography (eluted with 2:1 hexanes/acetone) to give 14 mg of the title compound. 1H NMR (500 MHz, CDCl3): δ 1.1-1.2 (1H, m), 1.6-1.9 (4H, m), 2.12 (1H, m), 2.42 (1H, t, J=10 Hz), 2.57 (1H, t, J=10 Hz), 3.4-3.6 (2H, m), 3.63 (1H, d, J=8.5 Hz), 5.6 (1H, br s), 6.84 (1H, d, J=5.5 Hz), 7.3-7.8 (7H, m), 7.88 (1H, d, J=7 Hz), 8.18 (1H, d, J=7 Hz), 8.41 (1H, d, J=5.5 Hz), 8.62 (1H, s). Mass spectrum (CI) 449.1 (M+1).

Provenance & Evidence