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

HRID 1685665Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1685665
[S:1](Cl)(=[O:4])(=[O:3])[NH2:2].C1(C)C=CC=CC=1.[OH:13][C:14]1[CH:15]=[C:16]([S:20][CH2:21][CH2:22][N:23]([N:32]2[CH:36]=[N:35][N:34]=[CH:33]2)[C:24]2[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=2)[CH:17]=[CH:18][CH:19]=1>O.C(OCC)(=O)C.CN(C)C(=O)C>[C:28]([C:27]1[CH:30]=[CH:31][C:24]([N:23]([N:32]2[CH:36]=[N:35][N:34]=[CH:33]2)[CH2:22][CH2:21][S:20][C:16]2[CH:15]=[C:14]([O:13][S:1](=[O:4])(=[O:3])[NH2:2])[CH:19]=[CH:18][CH:17]=2)=[CH:25][CH:26]=1)#[N:29]

Komponenten

7

Edukt 3

HCID 1140TolueneHCID 24499Chlorosulfamic acidHCID 219769104-{[2-(3-Hydroxy-phenylsulfanyl)-ethyl]-[1,2,4]triazol-4-yl-amino}-benzonitrile

Produkt 1

HCID 11538931Sulfamic Acid 3-{2-[(4-cyano-phenyl)-[1,2,4]triazol-4-yl-amino]-ethylsulfanyl}-phenyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

Sulphamoyl chloride solution in toluene (1.5 ml, 0.7 M, 1.05 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-{[2-(3-Hydroxy-phenylsulfanyl)-ethyl]-[1,2,4]triazol-4-yl-amino}-benzonitrile (CAB02149, 75 mg, 0.22 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 (1×20 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 (STX1014) was filtered off and dried under high vacuum. Yield: 79 mg (85%) light yellow powder. 1H-NMR (400 MHz, DMSO-d6) δ3.23 (t, J=7.0 Hz, 2H), 4.07 (t, J=7.0 Hz, 2H), 6.54 (d, J=8.9 Hz, 2H), 7.08-7.12 (m, 1H), 7.20-7.26 (m, 1H), 7.39 (dd, J=9.2, 9.2 Hz, 1H), 7.69 (d, J=8.9 Hz, 2H), 8.03 (s, 2H, —NH2), 8.94 (s, 2H); MS (FAB+): m/z 85.1.1 (28%), 417.0 (100%, [C17H16N6O3S2+H]+); HRMS (FAB+) for C17H17N6O3S2: 417.08036; Found, 417.08067; HPLC tR=1.53 min (99.7%).

Aufarbeitung

  1. additionwas added
  2. customthe organic layer was separated
  3. washwashed with water (2×30 ml) and brine (1×20 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 (STX1014) was filtered off
  9. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-58eeacfd73924f969f7b177c7e93b83f
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148415B2

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