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

HRID 1685650

Reaktionsgleichung

Reaktionsgleichung von HRID 1685650
[S:1](Cl)(=[O:4])(=[O:3])[NH2:2].C1(C)C=CC=CC=1.[F:13][C:14]1[CH:34]=[CH:33][C:17]([CH2:18][N:19]([C:25]2[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[CH:27][CH:26]=2)[N:20]2[CH:24]=[N:23][N:22]=[CH:21]2)=[CH:16][C:15]=1[OH:35]>O.C(OCC)(=O)C.CN(C)C(=O)C>[C:31]([C:28]1[CH:29]=[CH:30][C:25]([N:19]([CH2:18][C:17]2[CH:33]=[CH:34][C:14]([F:13])=[C:15]([O:35][S:1](=[O:4])(=[O:3])[NH2:2])[CH:16]=2)[N:20]2[CH:21]=[N:22][N:23]=[CH:24]2)=[CH:26][CH:27]=1)#[N:32]

Komponenten

7

Edukt 3

HCID 1140TolueneHCID 24499Chlorosulfamic acidHCID 167478394-[(4-Fluoro-3-hydroxybenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole

Produkt 1

HCID 11603462(5-{[(4-cyanophenyl)(4H-1,2,4-triazol-4-yl)amino]methyl}-2-fluorophenyl) sulfamate

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-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;

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 acetone (5 ml)
  7. customprecipitated by addition of diethyl ether
  8. filtrationThe precipitate (STX1122) was filtered off
  9. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-bbaa6a87282d42bf9829572495b7d756
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148415B2

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