Hydrochloric Acid → HCID 57732189, Verbindung

HRID 401745Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 401745
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.C([C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28](C)(C)[CH2:29][NH2:30])=[CH:23][CH:22]=1)(C)(C)C.[C:33](=[O:36])([O-])[O-].[Na+].[Na+].O.C(=O)([O-])[O-].[ClH:44]>C(=[Mo](=C=O)(=C=O)(=C=O)(=C=O)=C=O)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:44][C:21]1[CH:22]=[CH:23][C:24]([NH:27][CH2:28][CH2:29][NH:30][C:33](=[O:36])[C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]3[S:13][CH:14]=[CH:15][N:16]=3)(=[O:10])=[O:9])=[CH:4][CH:3]=2)=[CH:25][CH:26]=1

Komponenten

9

Edukt 6

HCID 313Hydrochloric AcidHCID 962WaterHCID 10340Sodium CarbonateHCID 19660Carbonate IonHCID 10193184-Iodo-N-(thiazol-2-yl)benzenesulfonamideHCID 68534592HCID 68534592, Verbindung

Produkt 1

HCID 57732189HCID 57732189, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 178521658HCID 178521658, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 4-iodo-N-1,3-thiazol-2-ylbenzenesulfonamide (Preparation 98, 0.2 g, 0.5 mmol), N-(2)-(4-tert-butyl-phenyl)-2-methyl-propane-1,2-diamine (0.55 g, 2.5 mmol), hexacarbonylmolybdenum (70 mg, 0.2 mmol), palladium(ii) acetate (6 mg, 0.02 mmol), and sodium carbonate (200 mg, 2 mmol) in water (1.5 mL, 83 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; 0.9 g, 2.50 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 mixture was filtered. The filtrate was concentrated in vacuo, and the residue was lyophilized from water/acetonitrile. The resulting solid was triturated with methylene chloride and ether. The resulting solid was purified via HPLC (Prep: Phenomenex 250×30.0 mm 15 micron C18 column. 40 mL/min. Gradient 15% B to 100% B over 25 min. Solvent A: 7800 water/200 acetonitrile/8 TFA. Solvent B: 7200 acetonitrile/800 water/8 TFA).

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. filtrationThe mixture was filtered
  10. concentrationThe filtrate was concentrated in vacuo
  11. customThe resulting solid was triturated with methylene chloride and ether
  12. customThe resulting solid was purified via HPLC (Prep: Phenomenex 250×30.0 mm 15 micron C18 column. 40 mL/min. Gradient 15% B to 100% B over 25 min. Solvent A: 7800 water/200 acetonitrile/8 TFA. Solvent B: 7200 acetonitrile/800 water/8 TFA)

Quellen und Nachweise

ORD-Eintrag
ord-4f6c717d19e54aa89adc774c73c3a970
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741934B2

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