Toluene → HCID 16749441, compound

HRID 901163Notes

Reaction equation

HRID 901163 reaction equation
[S:1](Cl)(=[O:4])(=[O:3])[NH2:2].C1(C)C=CC=CC=1.[Cl:13][C:14]1[CH:15]=[C:16]([CH:32]=[C:33]([O:36][CH3:37])[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>[Cl:13][C:14]1[CH:15]=[C:16]([CH2:17][N:18]([C:19]2[CH:20]=[CH:21][C:22]([C:23]#[N:24])=[CH:25][CH:26]=2)[N:27]2[CH:31]=[N:30][N:29]=[CH:28]2)[CH:32]=[C:33]([O:36][CH3:37])[C:34]=1[O:35][S:1](=[O:4])(=[O:3])[NH2:2]

Participants

7

Reactant 3

HCID 1140TolueneHCID 24499Chlorosulfamic acidHCID 16749115HCID 16749115, compound

Product 1

HCID 16749441HCID 16749441, 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-Chloro-4-hydroxy-5-methoxy-benzyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile (CAB02179, 212 mg, 0.596 mmol) was added to the colourless solution and the mixture was stirred for 18 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 (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: 219 mg (84%) white powder. 1H-NMR (400 MHz, d6-DMSO) δ=3.78 (s, 3H, —OCH3), 6.74 (d, J=9.0 Hz, 2H), 7.04 (d, J=2.0 Hz, 1H), 7.07 (d, J=2.0 Hz, 1H), 7.77 (d, J=9.0 Hz, 2H), 7.98 (s, 2H, —NH2), 8.91 (s, 2H). LRMS (FAB+): 435.0 (100, [M+H]+). HRMS (FAB+): 435.06476 C17H16N6O4SCl requires 435.064228.

Workup

  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

Sources & evidence

ORD record
ord-007af11d1bce4f16b0f37bac63e8c802
Source dataset
uspto-grants-2008_04
Patent number
US07361677B2

Reaction notes

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