Cyanamide → HCID 23525779, compound

Participants

Reaction Steps

To a solution of cyanamide (23.2 mg, 0.546 mmol) (Aldrich) in acetonitrile (2.5 mL) and tert-butanol (2.5 mL) was added [3-(4-Isothiocyanatophenoxy)-propyl]carbamic acid tert-butyl ester (from Example 64; 156.9 mg, 0.508 mmol) followed by a solution of potassium tert-butoxide (0.56 mL, 1 M in tert-BUOH). After 30 minutes at room temperature, 2-bromo-1-(3-fluoro-4-methoxy-phenyl)ethan-1-one (125.8 mg, 0.509 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)-carbamic acid tert-butyl ester (260.1 mg, 99% yield). HRMS, Observed: 517.1921; Calcd for M+H+:517.1916.

Provenance & Evidence