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

HRID 901135

Reaktionsgleichung

Reaktionsgleichung von HRID 901135
[S:1](Cl)(=[O:4])(=[O:3])[NH2:2].C1(C)C=CC=CC=1.[OH:13][C:14]1[CH:19]=[CH:18][C:17]([S:20][CH2:21][CH2:22][CH2:23][N:24]([N:33]2[CH:37]=[N:36][N:35]=[CH:34]2)[C:25]2[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][CH:26]=2)=[CH:16][CH:15]=1>O.C(OCC)(=O)C.CN(C)C(=O)C>[C:29]([C:28]1[CH:31]=[CH:32][C:25]([N:24]([N:33]2[CH:37]=[N:36][N:35]=[CH:34]2)[CH2:23][CH2:22][CH2:21][S:20][C:17]2[CH:18]=[CH:19][C:14]([O:13][S:1](=[O:4])(=[O:3])[NH2:2])=[CH:15][CH:16]=2)=[CH:26][CH:27]=1)#[N:30]

Komponenten

7

Edukt 3

HCID 1140TolueneHCID 24499Chlorosulfamic acidHCID 219768664-{[3-(4-Hydroxy-phenylsulfanyl)-propyl]-[1,2,4]triazol-4-yl-amino}-benzonitrile

Produkt 1

HCID 21044501Sulfamic Acid 4-{3-[(4-cyano-phenyl)-[1,2,4]triazol-4-yl-amino]-propylsulfanyl}-phenyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

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) δ=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]+).

Aufarbeitung

  1. additionwas added
  2. customthe organic layer was separated
  3. washwashed with water (2×30 mL) and brine (20 mL)
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in a small amount of acetone
  7. customprecipitated by addition of hexane
  8. filtrationThe precipitate was filtered off
  9. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-59d2e9d28d1b4165af3c8c659f72adc2
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07361677B2

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