Trifluoroacetic acid → HCID 20755351, compound

Participants

Reaction Steps

A solution of 4-[1-methyl-2,4-dioxo-6-(3-phenyl-prop-1-ynyl)-1,4-dihydro-2H-2λ4-benzo[1,2,6]thiadiazin-3-yl methyl]benzoic acid tert-butyl ester (0.33 g, 0.66 mmol) in methylene chloride (10 mL) was treated with trifluoroacetic acid (3 mL), and stirred at room temperature for 1 hour. The reaction mixture was evaporated to dryness, treated with hot ethyl acetate, allowed to cool, and the solid collected by filtration. The solid was triturated with ethyl ether, the solid collected by filtration, and allowed to air dry under house vacuum. The process afforded 0.03 g of 4-[1-methyl-2,4-dioxo-6-(3-phenyl-prop-1-ynyl)-1,4-dihydro-2H-2λ4-benzo[1,2,6]thiadiazin-3-yl methyl]benzoic acid as a blue/green solid (9.5% yield. 1H-NMR (CDCl3); d 8.30 (d, 1H), 8.08-8.06 (d, 2H), 7.69-7.67 (dd, 1H), 7.48-7.46 (d, 2H), 7.40-7.32 (m, 4H), 7.27-7.23 (m, 1H), 6.97-6.95 (d, 1H), 5.44-5.40 (d, 1H), 4.81-4.77 (d, 1H), 3.83 (s, 2H), 3.41 (s, 3H). MS: M++1=445.1 Da

Provenance & Evidence