Water → HCID 86604152, compound

Participants

Reaction Conditions

Reaction Steps

N,N-Dimethylaminopropyl thioguanidine dihydrochloride (1.71 mmol, 400 mg) was suspended in dry DCM and cooled to 0° C. under N2 atm. DIEA (6.0 mmol, 775 mg) was then added over 5 min. and the mixture stirred until it became homogeneous (5-10 min). A solution of 4-nitrobenzylchloroformate (2.05 mmol, 445 mg) in dry DCM (10 mL) was then added via syringe over 15 minutes and the resulting mixture was allowed to warm to rt overnight. The crude reaction mixture was then washed with DI water and 50% brine, dried over anhydrous Na2SO4, filtered, and concentrated. Purification of the resulting residue by column chromatography on silica get with 9:1 ACN:DI water afforded the desired product (106, 350 mg, 40% yield) as a white foamy solid.

Provenance & Evidence