Methanesulfonyl chloride → N-[5-(5-Cyanopyridin-3-ylethynyl)-2-fluorophenyl]-N-methanesulfonyl-methanesulfonamide
Reaction equation
[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]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 50 °C
Procedure
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%).
Workup
- 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)
Sources & evidence
- ORD record
- ord-094567534f3147359f544421396bb3f5
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07915424B2
Reaction notes
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