1-Hydroxybenzotriazole → Tert-butyl 2-[3-{1-(4-sulfamoylphenyl)-5-p-tolyl-1h-pyrazol-3-yl}propanamido]ethylcarbamate

Participants

Reaction Steps

a Celecox-Sulforhodamine Analog: Compound 30f was synthesized by the method outlined in FIG. 3. Briefly, Compound 30c as synthesized as set forth hereinabove. Compound 30c was then complexed with tert-butyl 2-aminoethylcarbamate for 16 hours at room temperature in the presence of 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (EDCl), 1-hydroxybenzotriazole (HOBt), and N,N-diisopropylethylamine (DIPEA) in mimethylformamide (DMF) to produce tert-butyl 2-[3-{1-(4-sulfamoylphenyl)-5-p-tolyl-1H-pyrazol-3-yl}propanamido]ethylcarbamate as a yellow solid (46% yield). This product was then dissolved in dichloromethane and treated with HCl (gas) for 2 hours at room temperature, producing N-(2-aminoethyl)-3-{1-(4-sulfamoylphenyl)-5-p-tolyl-1H-pyrazol-3-yl}propanamide hydrochloride as a yellow solid (80% yield).

Provenance & Evidence