1,3-Cyclopentanedione → 3-(3-Imidazo[1,2-a]pyridin-3-yl-phenylamino)-cyclopent-2-enone

HRID 1093525Notes

Reaction equation

HRID 1093525 reaction equation
[N:1]1[CH:2]=[C:3]([C:10]2[CH:11]=[C:12]([NH2:16])[CH:13]=[CH:14][CH:15]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[C:17]1(=O)[CH2:21][CH2:20][C:19](=[O:22])[CH2:18]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.CO>[N:1]1[CH:2]=[C:3]([C:10]2[CH:11]=[C:12]([NH:16][C:17]3[CH2:21][CH2:20][C:19](=[O:22])[CH:18]=3)[CH:13]=[CH:14][CH:15]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

6

Reactant 3

HCID 774661,3-CyclopentanedioneHCID 521998p-Toluenesulfonic acid monohydrateHCID 665926673-Imidazo[1,2-a]pyridin-3-yl-phenylamine

Product 1

HCID 665926013-(3-Imidazo[1,2-a]pyridin-3-yl-phenylamino)-cyclopent-2-enone

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

A solution of 3-imidazo[1,2-a]pyridin-3-yl-phenylamine (210 mg, 1.0 mmol), 1,3-cyclopentandione (110 mg, 1.1 mmol) and p-toluenesulfonic acid monohydrate (17 mg, 0.1 mmol) in toluene (2 ml) was stirred and heated at reflux under N2 for 8 hours. After cooling to RT the mixture was diluted with methanol (˜3 ml) then filtered. The solid was washed with Et2O then dried under vacuum to give the title compound. MS: [M+H]+ 290.

Workup

  1. temperatureheated
  2. temperatureat reflux under N2 for 8 hours
  3. filtrationthen filtered
  4. washThe solid was washed with Et2O
  5. customthen dried under vacuum

Sources & evidence

ORD record
ord-57bf35b29246490c99074179d1a348f7
Source dataset
uspto-grants-2012_03
Patent number
US08131527B1

Reaction notes

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