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

HRID 606957

Reaktionsgleichung

[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]([N:1]([S:20]([CH3:19])(=[O:22])=[O:21])[S:20]([CH3:19])(=[O:22])=[O:21])[CH:3]=2)[CH:12]=[N:13][CH:14]=1)#[N:17]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

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 (0.2 g, 1.9 mmol) in tetrahydrofuran to the reaction and heat at 50° C. for 16 h. 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 100:0 to 80:20 dichloromethane:ethyl acetate), to give the title compound as a white solid (114 mg, 36%).

Aufarbeitung

customto the reaction
concentrationConcentrate
dissolutiondissolve the crude
customreaction in ethyl acetate
washWash the organic layer with water
dry with materialan aqueous saturated solution of sodium chloride, dry (potassium carbonate)
filtrationfilter
concentrationconcentrate
custompurify
wash(silica gel chromatography, eluting with 100:0 to 80:20 dichloromethane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag: ord-094567534f3147359f544421396bb3f5
Quelldatensatz: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07915424B2

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