Toluene → HCID 58880275, compound

HRID 2358197Notes

Reaction equation

HRID 2358197 reaction equation
[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:9]=[C:8]([CH2:10][N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)[CH:7]=[C:6]([NH:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26]S(=O)(=O)N)=[C:22]([F:31])[CH:21]=2)(=[O:19])=[O:18])[CH:5]=1.S(Cl)(=O)(=O)N.C1(C)C=CC=CC=1.CCOC(C)=O>CC(N(C)C)=O.O>[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:9]=[C:8]([CH2:10][N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)[CH:7]=[C:6]([NH:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([F:31])[CH:21]=2)(=[O:18])=[O:19])[CH:5]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 24499Chlorosulfamic acidHCID 59389679HCID 59389679, compound

Product 1

HCID 58880275HCID 58880275, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

3-(3-Fluoro-4-sulfamoyloxy-benzenesulfonylamino)-5-[1,2,4]triazol-1-ylmethyl-benzoic acid methyl ester (CAB04128, STX1528): Sulphamoyl chloride solution in toluene (3 ml, 0.7 M, 2.1 mmol) was concentrated under reduced pressure. The residue was dissolved In DMA (5 ml) at 0° C. and CAB04122 (120 mg, 0.295 mmol) was added to the solution. Stirring was continued for 18 hours, EtOAc (50 ml) and water 30 ml were added, the organic layer was separated, washed with water (3×30 ml) and brine (20 ml), dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by flash chromatography on silica (chloroform/acetone 1:1) to give the title compound as a light yellow solid. Yield 86 mg (60%).

Workup

  1. additionCAB04122 (120 mg, 0.295 mmol) was added to the solution
  2. customthe organic layer was separated
  3. washwashed with water (3×30 ml) and brine (20 ml)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica (chloroform/acetone 1:1)

Sources & evidence

ORD record
ord-9087292e56184a7f957e800ccca21f59
Source dataset
uspto-grants-2010_07
Patent number
US07763642B2

Reaction notes

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