Ethyl Acetate → HCID 21186249, compound

Participants

Reaction Steps

2-(Trimethylsilyl)ethoxymethyl chloride (0.315 ml) was added dropwise to a stirred solution of 2-chloro-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (0.47 g) and N,N-diisopropylethylamine (0.347 ml) in dry DMF (7 ml) at -15° C. Stirring was continued for 40 minutes at this temperature after the addition was complete. Ethyl acetate (40 ml) was added and the mixture was washed with water (3×15 ml) and saturated sodium chloride solution and then dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by gradient elution with 0-30% ethyl acetate/hexane through a silica gel Mega Bond Elut column to give 2-chloro-N-(3-methoxy-5-methylpyrazin-2-yl)-N-[2-(trimethylsilyl)ethoxymethyl]pyridine-3-sulphonamide (0.462 g) as an oil; 1H NMR (CDCl3): 0.0 (s, 9 H), 0.85 (t, 2 H), 2.5 (s, 3 H), 3.75 (t, 2 H), 3.8 (s, 3 H), 5.3 (s, 2 H), 7.3 (dd, 1 H), 7.8 (s, 1 H), 8.4 (dd, 1 H), 8.5 (dd, 1 H); mass spectrum (+ve ESP): 403 (M+H)+.

Provenance & Evidence