Sodium Sulfate → 2-Methyl-5-(3-sulfamoyl-phenylamino)-thiazole-4-carboxylic acid (5-fluoro-pyridin-2-yl)-amide

HRID 2244441Notes

Reaction equation

HRID 2244441 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.C[Al](C)C.C([O:15][C:16]([C:18]1[N:19]=[C:20]([CH3:34])[S:21][C:22]=1[NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([S:30](=[O:33])(=[O:32])[NH2:31])[CH:25]=1)=O)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCOCC1.O>[F:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:16]([C:18]2[N:19]=[C:20]([CH3:34])[S:21][C:22]=2[NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([S:30](=[O:33])(=[O:32])[NH2:31])[CH:25]=2)=[O:15])=[N:3][CH:4]=1

Participants

7

Reactant 4

HCID 24436Sodium SulfateHCID 27377012-Amino-5-fluoropyridineHCID 16682925TrimethylaluminumHCID 675495532-Methyl-5-(3-sulfamoyl-phenylamino)-thiazole-4-carboxylic acid ethyl ester

Product 1

HCID 866065722-Methyl-5-(3-sulfamoyl-phenylamino)-thiazole-4-carboxylic acid (5-fluoro-pyridin-2-yl)-amideYield 3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-amino-5-fluoro pyridine (0.15 g, 1.38 mmol) in 10 ml dry dioxane was treated at 0° C. with trimethylaluminium (2M in hexane, 0.69 ml, 1.38 mmol). The mixture was stirred at room temperature for 1 h. 2-Methyl-5-(3-sulfamoyl-phenylamino)-thiazole-4-carboxylic acid ethyl ester (0.12 g, 0.35 mmol) was added and the reaction mixture was refluxed for 4 h. 1 ml water and 2 g sodium sulfate were sequentially added and filtered. The filtrate was evaporated and the residue purified by flash chromatography (hetane, ethyl acetate) to yield 2-methyl-5-(3-sulfamoyl-phenylamino)-thiazole-4-carboxylic acid (5-fluoro-pyridin-2-yl)-amide (0.004 g, 3%) as an off-white solid, MS (ISP): m/e=408.4 (M+H+).

Workup

  1. temperaturethe reaction mixture was refluxed for 4 h
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. customthe residue purified by flash chromatography (hetane, ethyl acetate)

Sources & evidence

ORD record
ord-c920d8fa2e7f4d0786bccd00a0afdddc
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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