Cyclopropanecarbonyl chloride → HCID 57385785, compound

HRID 1874571Notes

Reaction equation

HRID 1874571 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:30])[C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([C:28]#[N:29])([CH3:27])[CH3:26])[CH:20]=4)[CH:14]=[CH:15][CH:16]=3)=[CH:6][N:5]2[CH:31]=1.[CH:32]1([C:35](Cl)=[O:36])[CH2:34][CH2:33]1>CN(C)C(=O)C.C(OCC)(=O)C>[C:28]([C:25]([C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=1)[C:18]([NH:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([O:10][C:7]2[CH:8]=[CH:9][C:4]3[N:5]([CH:31]=[C:2]([NH:1][C:35]([CH:32]4[CH2:34][CH2:33]4)=[O:36])[N:3]=3)[CH:6]=2)[CH:12]=1)=[O:30])([CH3:27])[CH3:26])#[N:29]

Participants

5

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 57387818HCID 57387818, compound

Product 1

HCID 57385785HCID 57385785, compoundYield 43%

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-(1-cyano-1-methylethyl)benzamide (200 mg, 0.486 mmol) in N,N-dimethylacetamide (2.0 mL) was added cyclopropanecarbonyl chloride (46 μL, 0.510 mmol), and the mixture was stirred at room temperature for 8 hr. The reaction mixture was diluted with ethyl acetate (100 mL), washed with 5% aqueous sodium hydrogen carbonate solution (50 mL) and saturated brine (50 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 basic silica gel column chromatography (NH silica gel, hexane/ethyl acetate=50/50→0/100), and fractions containing the desired product were concentrated under reduced pressure. The residue was triturated with ethyl acetate and diisopropyl ether to give the title compound (100 mg, 43%) as a colorless solid.

Workup

  1. washwashed with 5% aqueous sodium hydrogen carbonate solution (50 mL) and saturated brine (50 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 basic silica gel column chromatography (NH silica gel, hexane/ethyl acetate=50/50→0/100), and fractions
  6. additioncontaining the desired product
  7. concentrationwere concentrated under reduced pressure
  8. customThe residue was triturated with ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-2630765f2dd64c8fbc413a08e4e5dd0e
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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