Triethylamine → HCID 10718457, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 100 mg (0.266 mmol) of the compound of Example 25 (previously dried at 60° C. under 0.1 mmHg for 18 h prior to use) and 88 mg (120 μL, 0.88 mmol) of triethylamine in 2 mL dichloromethane at 0° C. was treated with 85 mg (58 μL, 0.73 mmol) of methanesulfonyl chloride, followed by stirring at 0° C. for 30 min. The solution was diluted with dichloromethane and extracted with water (2×) and saturated sodium bicarbonate solution. Drying (Na2SO4) and concentration in vacuo afforded a solid which was dissolved in 2 mL DMF and treated via cannula to a 0° C. solution of 38 mg (0.40 mmol) of methanesulfonamide in 2 mL DMF which had been previously treated with 10 mg (17 mg of 60% in oil, 0.43 mmol) of sodium hydride. The solution was then warmed at 60° C. for 18 h. The solution was cooled and the DMF removed in vacuo, and the residue was dissolved in ethyl acetate and extracted with water (2×). Drying (Na2SO4) and concentration in vacuo afforded a solid which was subjected to radial chromatography on a 2 mm chromatotron plate, eluting with 1-4% (v/v) methanol in dichloromethane. These procedures afforded 31 mg (26%) of the title compound as a white solid. 1H NMR (CDCl3) δ 7.61, 7.56, 7.35, 7.23, 6.92, 6.81, 6.19, 6.06, 4.81, 4.29, 4.07, 3.82, 3.67, 3.22, 2.95, 2.62, 2.04, 1.90. ##STR5##

Provenance & Evidence