Water → 4-[(1,3-Thiazol-2-ylamino)sulfonyl]-N-(2-thienylmethyl)benzamide

HRID 1808166Notes

Reaction equation

HRID 1808166 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[S:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[CH2:22][NH2:23].[C:24](=O)([O-])[O-:25].[Na+].[Na+].O.C(=O)([O-])[O-]>Cl.C(=[Mo](=C=O)(=C=O)(=C=O)(=C=O)=C=O)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[S:13]1[CH:14]=[CH:15][N:16]=[C:12]1[NH:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([C:24]([NH:23][CH2:22][C:18]2[S:17][CH:21]=[CH:20][CH:19]=2)=[O:25])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

9

Reactant 5

HCID 962WaterHCID 10340Sodium CarbonateHCID 19660Carbonate IonHCID 34005(2-Thienylmethyl)amineHCID 10193184-Iodo-N-(thiazol-2-yl)benzenesulfonamide

Product 1

HCID 577322114-[(1,3-Thiazol-2-ylamino)sulfonyl]-N-(2-thienylmethyl)benzamide

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 178521658HCID 178521658, compoundCatalystHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
110 °C

Procedure

4-Iodo-N-1,3-thiazol-2-ylbenzenesulfonamide Preparation 98, 200 mg, 0.5 mmol), thiophene-2-methanamine (280 uL, 2.7 mmol), hexacarbonylmolybdenum (70 mg, 0.3 mmol), palladium(II) acetate (6 mg, 0.03 mmol), and sodium carbonate (170 mg, 1.6 mmol) in water (1.1 mL, 61 mmol) was heated 30 min at 110° C. in the microwave. The reaction mixture was diluted with 1 N HCl and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was dissolved in methylene chloride/MeOH and MP-Carbonate (2.73 mmol/g loading; 1.0 g, 2.73 mmol) was added. After stirring 1 h, LC/MS analysis indicated complete capture of the target compound. The resin was washed with methylene chloride then stirred in 8:1 methylene chloride/AcOH. LC/MS analysis indicated the target compound was released from the resin (not quantified). The material was further purified on the Isco (12 g SiO2, ethyl acetate to 4:1 ethyl acetate-MeOH).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in methylene chloride/MeOH
  7. washThe resin was washed with methylene chloride
  8. stirringthen stirred in 8:1 methylene chloride/AcOH
  9. customThe material was further purified on the Isco (12 g SiO2, ethyl acetate to 4:1 ethyl acetate-MeOH)

Sources & evidence

ORD record
ord-c277c6b241404fae86005725c479e7c1
Source dataset
uspto-grants-2013_01
Patent number
US08357711B2

Reaction notes

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