Toluene → HCID 10883602, compound

HRID 901168Notes

Reaction equation

HRID 901168 reaction equation
[S:1](Cl)(=[O:4])(=[O:3])[NH2:2].C1(C)C=CC=CC=1.[F:13][C:14]1[CH:15]=[C:16]([CH:32]=[CH:33][C:34]=1[OH:35])[CH2:17][N:18]([N:27]1[CH:31]=[N:30][N:29]=[CH:28]1)[C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=1>O.C(OCC)(=O)C.CN(C)C(=O)C>[C:23]([C:22]1[CH:21]=[CH:20][C:19]([N:18]([CH2:17][C:16]2[CH:32]=[CH:33][C:34]([O:35][S:1](=[O:4])(=[O:3])[NH2:2])=[C:14]([F:13])[CH:15]=2)[N:27]2[CH:28]=[N:29][N:30]=[CH:31]2)=[CH:26][CH:25]=1)#[N:24]

Participants

7

Reactant 3

HCID 1140TolueneHCID 24499Chlorosulfamic acidHCID 219769034-[(3-Fluoro-4-hydroxy-benzyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile

Product 1

HCID 10883602HCID 10883602, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

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-Fluoro-4-hydroxy-benzyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile (CAB03020, 220 mg, 0.71 mmol) was added to the colourless solution and the mixture was stirred for 4 h at room temperature. Ethyl acetate (50 mL) and water (30 mL) were added to the solution, the organic layer was separated, washed with water (2×25 mL) and brine (25 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 was filtered off and dried under high vacuum. Yield: 228 mg (83%) white powder. 1H-NMR (400 MHz, d6-DMSO) δ=5.11 (s, 2H), 6.71 (d, J=9.0 Hz, 2H), 7.23 (dd, 8.2, 1.2 Hz, 1H), 7.39 (dd, J=8.2, 8.2 Hz, 1H), 7.43 (dd, J=11.1, 2.1 Hz, 1H), 7.77 (d, J=9.0 Hz, 2H), 8.28 (s, 2H, —NH2), 8.92 (s, 2H). LRMS (FAB+): 389.1 (100, [M+H]+). HRMS (FAB+): 389.08298 C16H14N6O3SF requires 389.083214.

Workup

  1. additionwas added
  2. customthe organic layer was separated
  3. washwashed with water (2×25 mL) and brine (25 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 was filtered off
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-a2b6b4270abb4912959274f656100336
Source dataset
uspto-grants-2008_04
Patent number
US07361677B2

Reaction notes

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