Cyclopropanecarbonyl chloride → HCID 57749207, compound

HRID 1874563Notes

Reaction equation

HRID 1874563 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([O:10][C:11]3[CH:12]=[C:13]([NH:17][C:18](=[O:29])[C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=4)[CH:14]=[CH:15][CH:16]=3)=[CH:6][N:5]2[CH:30]=1.[CH:31]1([C:34](Cl)=[O:35])[CH2:33][CH2:32]1>CN(C)C(=O)C.C(OCC)(=O)C>[CH:31]1([C:34]([NH:1][C:2]2[N:3]=[C:4]3[CH:9]=[CH:8][C:7]([O:10][C:11]4[CH:12]=[C:13]([NH:17][C:18](=[O:29])[C:19]5[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:26])[F:27])[CH:20]=5)[CH:14]=[CH:15][CH:16]=4)=[CH:6][N:5]3[CH:30]=2)=[O:35])[CH2:33][CH2:32]1

Participants

5

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 68420860HCID 68420860, compound

Product 1

HCID 57749207HCID 57749207, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of N-{3-[(2-aminoimidazo[1,2-a]pyridin-6-yl)oxy]phenyl}-3-(trifluoromethyl)benzamide (300 mg, 0.727 mmol) in N,N-dimethylacetamide (3.0 mL) was added cyclopropanecarbonyl chloride (69 μL, 0.763 mmol), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate (200 mL), washed with 5% aqueous sodium hydrogen carbonate solution (100 mL) and saturated brine (100 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH silica gel, hexane/ethyl acetate=60/40→0/100), and fractions containing the desired product were concentrated under reduced pressure. The residue was triturated with ethyl acetate, diisopropyl ether and hexane to give the title compound (145 mg, 42%) as a colorless solid.

Workup

  1. washwashed with 5% aqueous sodium hydrogen carbonate solution (100 mL) and saturated brine (100 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationThe insoluble material was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (NH silica gel, hexane/ethyl acetate=60/40→0/100), and fractions
  6. additioncontaining the desired product
  7. concentrationwere concentrated under reduced pressure
  8. customThe residue was triturated with ethyl acetate, diisopropyl ether and hexane

Sources & evidence

ORD record
ord-9aeddd20ec9640c98befc17b165759dc
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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