Benzenesulfonamide, 3-amino- → HCID 25263014, compound

HRID 1897557Notes

Reaction equation

HRID 1897557 reaction equation
[C:1]([C:5]1[S:9][C:8]([C:10]([O-:12])=O)=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[Li+].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:38][C:39]1[CH:40]=[C:41]([S:45]([NH2:48])(=[O:47])=[O:46])[CH:42]=[CH:43][CH:44]=1>CN(C=O)C.O>[C:1]([C:5]1[S:9][C:8]([C:10]([NH:38][C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([S:45](=[O:47])(=[O:46])[NH2:48])[CH:40]=2)=[O:12])=[N:7][N:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 7377Benzenesulfonamide, 3-amino-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57659748HCID 57659748, compound

Product 1

HCID 25263014HCID 25263014, compoundYield 31.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of lithium 5-tert-butyl-1,3,4-thiadiazole-2-carboxylate (0.2 g, 1 mmol) and HATU (0.38 g, 1.0 mmol) in DMF (5 mL) was stirred at room temperature for 10 minutes, then 3-amino-benzenesulfonamide (0. 17 g, 1.0 mmol) was added. The reaction was stirred for four hours, diluted with water, and extracted with ethyl acetate. The combined extracts were washed with brine and water, dried over sodium sulfate, and evaporated. The residue was purified by column chromatography on silica gel with 0-5% methanol in dichloromethane to give 5-tert-butyl-N-(3-sulfamoylphenyl)-1,3,4-thiadiazole-2-carboxamide (107 mg, 31% yield). LC/MS: m/z 341.1 (M+H)+ at 2.79 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with brine and water
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel with 0-5% methanol in dichloromethane

Sources & evidence

ORD record
ord-bb8f33e6c4214d50b888995402127117
Source dataset
uspto-grants-2013_08
Patent number
US08519137B2

Reaction notes

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