Cyclopropylamine → HCID 57749171, compound

HRID 1874540Notes

Reaction equation

HRID 1874540 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]([C:20]4[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][N:21]=4)=[O:19])[CH:14]=[CH:15][CH:16]=3)=[CH:6][N:5]2[CH:27]=1.C([N:31]([CH2:35]C)[CH:32]([CH3:34])[CH3:33])(C)C.C(Cl)(=O)[O:38]CC(Cl)(Cl)Cl.C1(N)CC1>O1CCCC1.CN(C)C(=O)C>[CH:32]1([NH:31][C:35]([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]([C:20]5[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][N:21]=5)=[O:19])[CH:14]=[CH:15][CH:16]=4)=[CH:6][N:5]3[CH:27]=2)=[O:38])[CH2:33][CH2:34]1

Participants

7

Reactant 4

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 870632,2,2-Trichloroethyl chloroformateHCID 57749390N-{3-[(2-aminoimidazo[1,2-a]pyridin-6-yl)oxy]phenyl}-3-methylpyridine-2-carboxamide

Product 1

HCID 57749171HCID 57749171, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of N-{3-[(2-aminoimidazo[1,2-a]pyridin-6-yl)oxy]phenyl}-3-methylpyridine-2-carboxamide (129 mg, 0.359 mmol) and N,N-diisopropylethylamine (184 μL, 1.075 mmol) in tetrahydrofuran (5 mL) was added 2,2,2-trichloroethyl chlorocarbonate (52.0 μL, 0.378 mmol), and the mixture was stirred at room temperature for 30 min. Cyclopropaneamine (150 μL, 2.17 mmol) and N,N-dimethylacetamide (5 mL) were added to the reaction mixture, and the mixture was stirred at 80° C. for 22 hr. The reaction mixture was concentrated under reduced pressure, diluted with aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was washed with aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (0%→100% ethyl acetate-hexane) to give the title compound (20.3 mg, 13%) as a white solid.

Workup

  1. stirringthe mixture was stirred at 80° C. for 22 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additiondiluted with aqueous sodium hydrogen carbonate solution
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with aqueous sodium hydrogen carbonate solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltrated
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (0%→100% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-1e8fa758ea0c4370bc77836538db13ae
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

Loading…