HCID 19592319, compound → HCID 19592928, compound

HRID 613526Notes

Reaction equation

HRID 613526 reaction equation
[Cl:1][C:2]1[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[C:12]2[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH:24][C:25]([C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)=O)=[O:5]>C(O)(=O)C>[Cl:1][C:2]1[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[C:12]2[N:17]1[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N:24]=[C:25]1[C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)=[O:5]

Participants

3

Reactant 1

HCID 19592319HCID 19592319, compound

Product 1

HCID 19592928HCID 19592928, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 8-(2,6-dichlorobenzoylamino)-4-[2-(3-pyridinecarboxamido)phenylamino]quinoline (150 mg) in acetic acid was refluxed for 60 hours. After cooling, the mixture was concentrated in vacuo and diluted with ethyl acetate. The solution was washed with saturated sodium bicarbonate solution, dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from acetonitrile and collected by filtration to give 8-(2,6-dichlorobenzoylamino)-4-[2-(3-pyridyl)-1H-benzimidazol-1-yl]quinoline (136 mg).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated in vacuo
  3. additiondiluted with ethyl acetate
  4. washThe solution was washed with saturated sodium bicarbonate solution
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was crystallized from acetonitrile
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-f20b02b6866f45748a24d3df1e544f25
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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