Pyridine → HCID 17981729, compound

Participants

Reaction Conditions

Reaction Steps

Add dry pyridine (234 mL, 2.94 moles) to a cold (0° C.) solution of N-[methyl] N-[methoxy] 3,4-diaminobenzamide (135 g, 0.69 moles) in 1 liter of dry dichloromethane under a nitrogen atomosphere. Add isopropylsulfonyl chloride (85.4 mL, 0.76 moles) at 0° C. over 30 minutes, stir the mixture 0° C. for another 30 minutes, and then at room temperature overnight. Concentrate the reaction mixture under reduced pressure and partition the residue with diethyl ether (1 L) and 5 N hydrochloric acid (1 L). Separate the layers, discard the diethyl ether layer, add ethyl acetate (1.5 L) to the aqueous layer and stir while adding solid sodium carbonate until pH=6.5. Extract the aqueous layer using ethyl acetate, wash the combined organic layers, dry over magnesium sulfate and concentrate under reduced pressure. Subject the residue to silica gel chromatography eluting with a gradient 65:3 ethyl acetate:hexane to 100% ethyl acetate to provide a 40% yield of the desired compound.

Provenance & Evidence