Cyclopropanecarbonyl chloride → HCID 86644691, compound
Reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:10]([C:11]#[N:12])=[C:9]([O:13][C:14]3[C:15]([Cl:28])=[CH:16][C:17]([F:27])=[C:18]([NH:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])[CH:19]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH:29]1([C:32](Cl)=[O:33])[CH2:31][CH2:30]1>N1C=CC=CC=1>[Cl:28][C:15]1[CH:16]=[C:17]([F:27])[C:18]([NH:20][C:21](=[O:26])[C:22]([F:23])([F:25])[F:24])=[CH:19][C:14]=1[O:13][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([NH:1][C:32]([CH:29]3[CH2:31][CH2:30]3)=[O:33])[S:3][C:4]=2[C:10]=1[C:11]#[N:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of N-{5-[(2-amino-7-cyano-1,3-benzothiazol-6-yl)oxy]-4-chloro-2-fluorophenyl}-2,2,2-trifluoroacetamide (0.7 g, 1.63 mmol) in pyridine (3 mL) was added cyclopropanecarbonyl chloride (191 μL, 2.11 mmol), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate (100 mL), washed successively with 5% aqueous sodium hydrogen carbonate solution (100 mL) and saturated brine (100 mL), and dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=20/80→80/20), and the obtained solution was concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to give the title compound (348 mg, 43%) as a white powder.