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

HRID 2095886Notes

Reaction equation

HRID 2095886 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:27])[O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[C:13]([F:28])[CH:12]=3)=[CH:6][N:5]2[CH:29]=1.[CH:30]1([C:33](Cl)=[O:34])[CH2:32][CH2:31]1.O.C(=O)([O-])O.[Na+]>CN(C)C(=O)C>[CH:30]1([C:33]([NH:1][C:2]2[N:3]=[C:4]3[CH:9]=[CH:8][C:7]([O:10][C:11]4[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:27])[O:19][CH2:20][C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)=[C:13]([F:28])[CH:12]=4)=[CH:6][N:5]3[CH:29]=2)=[O:34])[CH2:32][CH2:31]1

Participants

6

Reactant 4

HCID 962WaterHCID 77637Cyclopropanecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 58158524Benzyl {4-[(2-aminoimidazo[1,2-a]pyridin-6-yl)oxy]-2-fluorophenyl}carbamate

Product 1

HCID 58158453Benzyl [4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)-2-fluorophenyl]carbamateYield 68.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of benzyl {4-[(2-aminoimidazo[1,2-a]pyridin-6-yl)oxy]-2-fluorophenyl}carbamate (12.1 g, 30.9 mmol) in N,N-dimethylacetamide (84.7 mL) was added cyclopropanecarbonyl chloride (3.36 mL, 37.0 mmol) at 0° C., and the mixture was stirred at room temperature for 2 hr. Water and saturated aqueous sodium hydrogen carbonate were 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 ethyl acetate and collected by filtration to give the title compound (9.7 g, 68%) 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 ethyl acetate
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-f6cbe3d4bd734a5baf199d3b9e6ec116
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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