Triethylamine → 4-[(5-Chloropyridin-2-yl)methoxy]-2,5-difluoro-N-(methylsulfonyl)benzamide diethylamine salt

HRID 512029Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 512029
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][OH:9])=[N:6][CH:7]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[F:28][C:29]1[CH:41]=[C:40](O)[C:39]([F:43])=[CH:38][C:30]=1[C:31]([NH:33][S:34]([CH3:37])(=[O:36])=[O:35])=[O:32]>ClCCl.CS(C)=O.O>[CH2:5]([NH:6][CH2:7][CH3:2])[CH3:4].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][C:40]2[C:39]([F:43])=[CH:38][C:30]([C:31]([NH:33][S:34]([CH3:37])(=[O:36])=[O:35])=[O:32])=[C:29]([F:28])[CH:41]=2)=[N:6][CH:7]=1

Komponenten

9

Edukt 5

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 20537893(5-Chloropyridin-2-yl)methanolHCID 580424162,5-difluoro-4-hydroxy-N-(methylsulfonyl)benzamide

Produkt 1

HCID 866825674-[(5-Chloropyridin-2-yl)methoxy]-2,5-difluoro-N-(methylsulfonyl)benzamide diethylamine salt

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (5-chloropyridin-2-yl)methanol (15 mg, 0.105 mmol), in dichloromethane (5 mL) and triethylamine (0.02 mL, 0.157 mmol) was added methanesulfonyl chloride (0.01 mL, 0.115 mmol). The reaction was stirred at room temperature for 2 hours. The solvent was removed in vacuo to afford a residue, which was taken up in DMSO (5 mL). Potassium carbonate (43 mg, 0.315 mmol) was added, followed by 2,5-difluoro-4-hydroxy-N-(methylsulfonyl)benzamide (Preparation 110, 29 mg, 0.115 mmol) and the reaction was heated to 50° C. overnight. The reaction mixture was cooled to room temperature, diluted with water (10 mL) and extracted with ethyl acetate (3×10 mL). The combined organic layers were dried over sodium sulphate, filtered and concentrated in vacuo. The resulting residue was purified by preparative HPLC to afford the title compound.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customto afford a residue, which
  3. temperaturethe reaction was heated to 50° C. overnight
  4. temperatureThe reaction mixture was cooled to room temperature
  5. extractionextracted with ethyl acetate (3×10 mL)
  6. dry with materialThe combined organic layers were dried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-3f891cc096084a35aafa378cfe49e8d8
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102621B2

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