Triethylamine → N-(3-aminosulfonyl-4-chloro-2-hydroxyphenyl)-N'-(3-methylisoxazol-4-yl)urea

Participants

Reaction Conditions

Reaction Steps

Under Ar, the mixture of 3-methylisoxazole-4-carboxylic acid (100 mg, 0.79 mmol) in 2 mL of N,N-dimethyl-formamide was heated to 80° C. Diphenylphosphoryl azide (216 mg, 0.79 mmol) and triethyl amine (0.11 mL, 0.79 mmol) were added. The resulting mixture was heated for another 2 hours when kept temperature at 80° C. The mixture was cooled to room temperature, a solution of 3-amino-6-chloro-2-hydroxybenzenesulfonamide (176 mg, 0.79 mmol) in 1 mL of N,N-dimethyl-formamide then added. The mixture was stirred for 18 hours at room temperature. Purification upon Gilson HPLC, eluting with acetonitrile/water (10/90, v/v to 90/10, v/v, over 10 min), gave the desired product (43 mg, 16%). LC-MS (m/z) 347.0 (M+).

Provenance & Evidence