Water → HCID 57732211, Verbindung

HRID 401746

Reaktionsgleichung

Reaktionsgleichung von HRID 401746
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]

Komponenten

9

Edukt 5

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

Produkt 1

HCID 57732211HCID 57732211, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 178521658HCID 178521658, VerbindungKatalysatorHCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-3bbfcf8b344b4897a6009febe1fcff52
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741934B2

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