Cyclopropanecarbonyl chloride → N-(7-cyano-6-{3-[(trifluoroacetyl)amino]phenoxy}-1,3-benzothiazol-2-yl)cyclopropanecarboxamide

HRID 1097449Notes

Reaction equation

HRID 1097449 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[CH:15]=[C:16]([NH:20][C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])[CH:17]=[CH:18][CH:19]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH:27]1([C:30](Cl)=[O:31])[CH2:29][CH2:28]1>N1C=CC=CC=1>[C:11]([C:10]1[C:4]2[S:3][C:2]([NH:1][C:30]([CH:27]3[CH2:29][CH2:28]3)=[O:31])=[N:6][C:5]=2[CH:7]=[CH:8][C:9]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21](=[O:26])[C:22]([F:25])([F:23])[F:24])[CH:15]=1)#[N:12]

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 86644683N-{3-[(2-amino-7-cyano-1,3-benzothiazol-6-yl)oxy]phenyl}-2,2,2-trifluoroacetamide

Product 1

HCID 86644684N-(7-cyano-6-{3-[(trifluoroacetyl)amino]phenoxy}-1,3-benzothiazol-2-yl)cyclopropanecarboxamideYield 71.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of N-{3-[(2-amino-7-cyano-1,3-benzothiazol-6-yl)oxy]phenyl}-2,2,2-trifluoroacetamide (1.5 g, 3.96 mmol) in pyridine (4 mL) was added cyclopropanecarbonyl chloride (467 μL, 5.15 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 (200 mL), washed successively with 5% aqueous sodium hydrogen carbonate solution (200 mL) and saturated brine (200 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=30/70→60/40), and the obtained solution was concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to give the title compound (1.26 g, 63%) as a colorless powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionThe obtained residue was diluted with ethyl acetate (200 mL)
  3. washwashed successively with 5% aqueous sodium hydrogen carbonate solution (200 mL) and saturated brine (200 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationInsoluble material was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=30/70→60/40)
  8. concentrationthe obtained solution was concentrated under reduced pressure
  9. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-aa6415907d854cf19b18402eb28a423f
Source dataset
uspto-grants-2012_03
Patent number
US08143258B2

Reaction notes

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