Toluene → (5-{[(4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino]methyl}-2-fluorophenyl) sulfamate

Participants

Reaction Steps

Sulphamoyl chloride solution in toluene (3 ml, 0.7 M, 2.1 mmol) was concentrated under reduced pressure (30° C. water bath temperature) to ca. 0.5 ml volume. The residue was cooled to 0° C. (ice bath) and N,N-dimethyl acetamide (5 ml) was added. 4-[(4-Fluoro-3-hydroxybenzyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile (STX488, 155 mg, 0.50 mmol) was added to the colourless solution and the mixture was stirred for 4 hours at room temperature. Ethyl acetate (50 ml) and water (30 mL) were added to the solution, the organic layer was separated, washed with water (2×30 ml) and brine (1×20 ml), dried over sodium sulphate and concentrated under reduced pressure. The residue was dissolved in acetone (5 ml) and precipitated by addition of diethyl ether. The precipitate (STX1122) was filtered off and dried under high vacuum. Yield: 157 mg (83%) white powder. 1H-NMR (400 MHz, DMSO-d6) δ5.07 (s, 2H), 6.74 (d, J=8.9 Hz, 2H), 7.20-7.26 (m, 1H), 7.33 (dd, J=10.1, 8.6 Hz, 1H), 7.38 (dd, J=7.4, 2.3 Hz, 1H), 7.75 (d, J=8.9 Hz, 2H), 8.25 (s, 2H, —NH2), 8.77 (s, 2H); MS (FAB+): m/z 389.0 (100%, [C16H13FN6O3S2+H]+); HRMS (FAB+) for C16H14FN6O3S: 389.08321; found, 389.08300; HPLC tR=1.763 min (100%); Anal. (C16H13FN6O3S) C, H, N;

Provenance & Evidence