Hydrochloric Acid → HCID 56597926, Verbindung

HRID 509097Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 509097
[F:1][C:2]1[CH:3]=[C:4]([SH:9])[CH:5]=[CH:6][C:7]=1[F:8].C(=O)([O-])[O-].[K+].[K+].[C:16]([C:18]1[CH:19]=[C:20]([S:25]([N:28](CC2C=CC(OC)=CC=2OC)[C:29]2[S:33][N:32]=[CH:31][N:30]=2)(=[O:27])=[O:26])[CH:21]=[CH:22][C:23]=1F)#[N:17].Cl>CN(C)C(=O)C.O1CCOCC1.CS(C)=O>[C:16]([C:18]1[CH:19]=[C:20]([S:25]([NH:28][C:29]2[S:33][N:32]=[CH:31][N:30]=2)(=[O:27])=[O:26])[CH:21]=[CH:22][C:23]=1[S:9][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=1)#[N:17]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27783783,4-DifluorobenzenethiolHCID 580422543-cyano-N-(2,4-dimethoxybenzyl)-4-fluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide

Produkt 1

HCID 56597926HCID 56597926, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 312751,4-DioxaneLösungsmittel2×HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

3,4-Difluorothiophenol (0.101 g, 0.690 mmol) and potassium carbonate (0.200 g, 1.45 mmol) were stirred in N,N-dimethylacetamide (3 mL). After 5 minutes, 3-cyano-N-(2,4-dimethoxybenzyl)-4-fluoro-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide (Preparation 1, 0.300 g, 0.690 mmol) was added to the reaction mixture and the mixture stirred at ambient temperature overnight. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with a 1M aqueous solution of sodium hydroxide, followed by brine, then dried over MgSO4, filtered and concentrated in vacuo to give a white solid. The solid was then dissolved in 1,4-dioxane and a 4M solution of hydrogen chloride in 1,4-dioxane (3 mL) added. The reaction mixture was stirred at ambient temperature overnight. The reaction mixture was concentrated in vacuo to give a residue. The residue was solubilised in dimethylsulfoxide (1 mL) and purified by the B-HPLC method to afford the title compound.

Aufarbeitung

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with a 1M aqueous solution of sodium hydroxide
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a white solid
  7. stirringThe reaction mixture was stirred at ambient temperature overnight
  8. concentrationThe reaction mixture was concentrated in vacuo
  9. customto give a residue
  10. custompurified by the B-HPLC method

Quellen und Nachweise

ORD-Eintrag
ord-ffd6c397771240408816e25c569d131f
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096558B2

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