反応 #48182

反応方程式

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

溶媒

water

Ethyl acetate

N,N-dimethylacetamide

water

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   その他the organic layer was separated
3. 3
   洗浄washed with water (2×30 mL) and brine (20 mL)
4. 4
   乾燥dried over sodium sulphate
5. 5
   濃縮concentrated under reduced pressure
6. 6
   workup.DISSOLUTIONThe residue was dissolved in a small amount of acetone
7. 7
   その他precipitated by addition of hexane
8. 8
   ろ過The precipitate was filtered off
9. 9
   その他dried under high vacuum

実験手順

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]+).

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