Phthalaldehyde → N-{6-[3-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)phenoxy]imidazo[1,2-a]pyridin-2-yl}cyclopropanecarboxamide

HRID 1874555Notes

Reaction equation

HRID 1874555 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH:12]=[C:13]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])[N:14]=2)[CH:11]=1.[C:24]1([CH:32]=O)[C:25]([CH:30]=[O:31])=[CH:26][CH:27]=[CH:28][CH:29]=1>C(O)(=O)C>[O:31]=[C:30]1[C:25]2[C:24](=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:32][N:1]1[C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH:12]=[C:13]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])[N:14]=2)[CH:11]=1

Participants

4

Reactant 2

HCID 4807PhthalaldehydeHCID 57749361N-[6-(3-aminophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide

Product 1

HCID 57749302N-{6-[3-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)phenoxy]imidazo[1,2-a]pyridin-2-yl}cyclopropanecarboxamideYield 18%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-[6-(3-aminophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (19.7 mg, 0.064 mmol), benzene-1,2-dicarbaldehyde (10.7 mg, 0.080 mmol) and acetic acid (4.0 mL) was stirred at 100° C. for 13 hr. The reaction mixture was concentrated under reduced pressure, and ethyl acetate was added to the residue. The mixture was washed with aqueous sodium hydrogen carbonate solution and saturated brine. The organic layer was concentrated, and the residue was purified by preparative HPLC to give the title compound (4.8 mg, 18%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and ethyl acetate
  2. additionwas added to the residue
  3. washThe mixture was washed with aqueous sodium hydrogen carbonate solution and saturated brine
  4. concentrationThe organic layer was concentrated
  5. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-2949d892ffaf4626bd4349bd0ad24ca1
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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