Tetrahydrofuran → HCID 56603230, compound

HRID 1852497Notes

Reaction equation

HRID 1852497 reaction equation
O1CCCC1.[NH2:6][C:7]1[C:15]([NH:16][C:17]2[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=2)[C:20]#[N:21])=[CH:14][CH:13]=[C:12]2[C:8]=1[CH2:9][CH2:10][CH2:11]2.[C:25](Cl)(=[O:30])[CH2:26][C:27](Cl)=[O:28]>CO>[C:20]([C:19]1[CH:18]=[C:17]([N:16]2[C:27](=[O:28])[CH2:26][C:25](=[O:30])[NH:6][C:7]3[C:8]4[CH2:9][CH2:10][CH2:11][C:12]=4[CH:13]=[CH:14][C:15]2=3)[CH:24]=[CH:23][CH:22]=1)#[N:21]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 74269Propanedioyl dichlorideHCID 86689312HCID 86689312, compound

Product 1

HCID 56603230HCID 56603230, compoundYield 29.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a dry tetrahydrofuran (75 mL) solution of 3-(4-aminoindan-5-ylamino)benzonitrile (0.75 g, 3.00 mmol) was added malonyl chloride (0.35 mL, 3.60 mmol) while stirring in ice-bath. The mixture was stirred under cooling in ice-bath for 1 hour and at room temperature for 1 hour. To the mixture was added methanol (5 mL) while stirring in ice-bath. The mixture was stirred under cooling in ice-bath for 1 hour and at room temperature for 1 hour. To the reaction mixture was added methanol (25 mL) while stirring in ice-bath. The mixture was stirred under cooling in ice-bath for 1 hour and at room temperature for 1 hour. The solvent was removed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/1-4/1) to slightly yellow crystal (0.40 g). The crystal was recrystallized from ethyl acetate to give the titled compound as white crystal (0.28 g, yield 29%).

Workup

  1. stirringThe mixture was stirred
  2. temperatureunder cooling in ice-bath for 1 hour
  3. stirringwhile stirring in ice-bath
  4. stirringThe mixture was stirred
  5. temperatureunder cooling in ice-bath for 1 hour
  6. waitat room temperature for 1 hour
  7. stirringwhile stirring in ice-bath
  8. stirringThe mixture was stirred
  9. temperatureunder cooling in ice-bath for 1 hour
  10. waitat room temperature for 1 hour
  11. customThe solvent was removed by evaporation under reduced pressure
  12. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/1-4/1) to slightly yellow crystal (0.40 g)
  13. customThe crystal was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-51344dfa199e4eabbd30f74ecfec321e
Source dataset
uspto-grants-2015_02
Patent number
US08962613B2

Reaction notes

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