Cyclopropanecarbonyl chloride → HCID 86644691, compound

HRID 1097477Notes

Reaction equation

HRID 1097477 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

HCID 77637Cyclopropanecarbonyl chlorideHCID 86644690HCID 86644690, compound

Product 1

HCID 86644691HCID 86644691, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionThe obtained residue was diluted with ethyl acetate (100 mL)
  3. washwashed successively with 5% aqueous sodium hydrogen carbonate solution (100 mL) and saturated brine (100 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=20/80→80/20)
  8. concentrationthe obtained solution was concentrated under reduced pressure
  9. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-39ffd8f502654bbeacc273f850aa9010
Source dataset
uspto-grants-2012_03
Patent number
US08143258B2

Reaction notes

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