Cyclopropanecarbonyl chloride → Benzyl [4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)phenyl]carbamate

HRID 2095881Notes

Reaction equation

HRID 2095881 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([O:10][C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:20])[OH:19])=[CH:13][CH:12]=3)=[CH:6][N:5]2[CH:21]=1.[CH2:22](NC(=O)O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH:33]1([C:36](Cl)=[O:37])[CH2:35][CH2:34]1.C(=O)([O-])O.[Na+]>CN(C)C(=O)C>[CH:33]1([C:36]([NH:1][C:2]2[N:3]=[C:4]3[CH:9]=[CH:8][C:7]([O:10][C:11]4[CH:12]=[CH:13][C:14]([NH:17][C:18](=[O:19])[O:20][CH2:22][C:23]5[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=5)=[CH:15][CH:16]=4)=[CH:6][N:5]3[CH:21]=2)=[O:37])[CH2:35][CH2:34]1

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 66969002Benzylcarbamate {4-[(2-aminoimidazo[1,2-a]pyridin-6-yl)oxy]phenyl}carbamate

Product 1

HCID 58158632Benzyl [4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)phenyl]carbamateYield 87%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of benzylcarbamate {4-[(2-aminoimidazo[1,2-a]pyridin-6-yl)oxy]phenyl}carbamate (8.7 g, 22.2 mmol) in N,N-dimethylacetamide (70 mL) was added cyclopropanecarbonyl chloride (2.21 mL, 24.4 mmol) at room temperature, and the mixture was stirred at room temperature for 1 hr. Saturated aqueous sodium hydrogen carbonate was added to the reaction mixture, and the mixture was extracted with ethyl acetate/tetrahydrofuran. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, and the residue was washed with hexane/ethyl acetate (=1/1) and collected by filtration to give the title compound (8.5 g, 87%) as a thin-brown solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate/tetrahydrofuran
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. washthe residue was washed with hexane/ethyl acetate (=1/1)
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-a6875b56e8f046dcafee69df050839ac
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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