Dimethyl Sulfoxide → 11-Cyclopropyl-6,11-dihydro-6-oxo-5H-dipyrido[3,2-b:2',3'-e][1,4]diazepine-4-carboxaldehyde

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Reaction Steps

To a solution of oxalyl chloride (0.08 g, 0.6 mmol) in methylene chloride (5 mL) cooled under Argon to -60° C. was added dropwise dimethyl sulfoxide (0.093 g, 1.2 mmol). After 2 minutes 11-cyclopropyl-5,11-dihydro-4-hydroxymethyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.15 g, 0.53 mmol) in dimethyl sulfoxide/methylene chloride (5 mL) was added dropwise and stirring was continued for an additional 15 minutes. Triethylamine (0.267 g, 2.6 mmol) was added and after 5 minutes the mixture was allowed to warm to room temperature. Water (5 mL) was added and the aqueous phase was separated and extracted with methylene chloride. The combined organic phase was dried and evaporated. Column chromatography over silica gel with 30% ethyl acetate/hexane gave the title compound, which crystallized from ethyl acetate/hexane. Yield 0.045 g, m.p. 220°-222° C.

Provenance & Evidence