Reaction #48182

Reaction equation

Sulphamoyl chloride

toluene

4-{[3-(4-hydroxy-phenylsulfanyl)-propyl]-[1,2,4]triazol-4-yl-amino}-benzonitrile

→

Sulfamic Acid 4-{3-[(4-cyano-phenyl)-[1,2,4]triazol-4-yl-amino]-propylsulfanyl}-phenyl Ester

Solvents

water

Ethyl acetate

N,N-dimethylacetamide

water

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   Otherthe organic layer was separated
3. 3
   Washwashed with water (2×30 mL) and brine (20 mL)
4. 4
   Dryingdried over sodium sulphate
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   workup.DISSOLUTIONThe residue was dissolved in a small amount of acetone
7. 7
   Otherprecipitated by addition of hexane
8. 8
   FiltrationThe precipitate was filtered off
9. 9
   Otherdried under high vacuum

Procedure

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-dimethylacetamide (5 mL) was added. 4-{[3-(4-hydroxy-phenylsulfanyl)-propyl]-[1,2,4]triazol-4-yl-amino}-benzonitrile (CAB02182, 140 mg, 0.40 mmol) was added to the colourless solution and the mixture was stirred for 18 hours at room temperature. Ethyl acetate (50 mL) and water (50 mL) were added to the solution, the organic layer was separated, washed with water (2×30 mL) and brine (20 mL), dried over sodium sulphate and concentrated under reduced pressure. The residue was dissolved in a small amount of acetone and precipitated by addition of hexane. The precipitate was filtered off and dried under high vacuum. Yield: 139 mg (81%) light yellow powder. 1H-NMR (400 MHz, d6-DMSO)=1.74 (tt, J=7.0, 7.0 Hz, 2H), 3.97 (t, J=7.0 Hz, 2H), 6.62 (d, J=9.0 Hz, 2H), 7.22 (d, J=8.6 Hz, 2H), 7.43 (d, J=8.6 Hz, 2H), 7.74 (d, J=9.0 Hz, 2H), 8.03 (s, 2H, —NH2), 9.00 (s, 2H). LRMS (FAB+): 431.1 (100, [M+H]+).

Source