Methanesulfonyl chloride → N-[5-(5-Cyanopyridin-3-ylethynyl)-2-fluorophenyl]-methanesulfonamide

HRID 606956

Reaktionsgleichung

Reaktionsgleichung von HRID 606956
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]#[C:10][C:11]2[CH:12]=[N:13][CH:14]=[C:15]([CH:18]=2)[C:16]#[N:17])[CH:5]=[CH:6][C:7]=1[F:8].[CH3:19][S:20](Cl)(=[O:22])=[O:21]>N1C=CC=CC=1.O1CCCC1.O>[C:16]([C:15]1[CH:18]=[C:11]([C:10]#[C:9][C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([NH:1][S:20]([CH3:19])(=[O:22])=[O:21])[CH:3]=2)[CH:12]=[N:13][CH:14]=1)#[N:17]

Komponenten

6

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 670478225-(3-Amino-4-fluorophenylethynyl)-nicotinonitrile

Produkt 1

HCID 67047582N-[5-(5-Cyanopyridin-3-ylethynyl)-2-fluorophenyl]-methanesulfonamideAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Dissolve 5-(3-amino-4-fluorophenylethynyl)-nicotinonitrile, (prepared as described in EXAMPLE 160), (0.2 g, 0.8 mmol) in anhydrous pyridine. Add a solution of methanesulfonyl chloride (0.1 g, 0.88 mmol) in tetrahydrofuran to the reaction and stir overnight at room temperature. Concentrate and dissolve the crude reaction in ethyl acetate and water. Wash the organic layer with water, an aqueous saturated solution of sodium chloride, dry (potassium carbonate), filter, concentrate and purify (silica gel chromatography, eluting with 95:5 to 80:20 dichloromethane:ethyl acetate), to give the title compound as a tan solid (50 mg, 20%).

Aufarbeitung

  1. customto the reaction
  2. concentrationConcentrate
  3. dissolutiondissolve the crude
  4. customreaction in ethyl acetate
  5. washWash the organic layer with water
  6. dry with materialan aqueous saturated solution of sodium chloride, dry (potassium carbonate)
  7. filtrationfilter
  8. concentrationconcentrate
  9. custompurify
  10. wash(silica gel chromatography, eluting with 95:5 to 80:20 dichloromethane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-e162a1bfde0440e4a4d47b5a19036340
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915424B2

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