Cyanamide → HCID 23525780, compound

Participants

Reaction Steps

To a solution of cyanamide (21.2 mg, 0.499 mmol) (Aldrich) in acetonitrile (2.5 mL) and tert-butanol (2.5 mL) was added ethyl-[3-(4-isothiocyanato-phenoxy)propyl]carbamic acid tert-butyl ester (153.8 mg, 0.4571 mmol from Example 66, step C) followed by a solution of potassium tert-butoxide (0.50 mL, 1 M in tert-butanol) (Aldrich). After 30 minutes at room temperature, 2-bromo-1-(3-fluoro-4-methoxyphenyl)ethan-1-one (112.5 mg, 0.4553 mmol) (Maybridge Chemical) was added. The reaction mixture was stirred at room temperature for 1 hour and then heated at 75° C. for 2 hours. The resulting mixture was poured into water (10 mL). The product was collected by filtration, washed with diethyl ether and dried in vacuo to provide (3-[4-[4-Amino-5-(3-fluoro-4-methoxy-benzoyl)-thiazol-2-ylamino]-phenoxy]-propyl)-ethyl-carbamic acid tert-butyl ester (245.1.6 mg, 99% yield). HRMS, observed: 545.2230; Calcd for M+H: 545.2229.

Provenance & Evidence