Dimethylformamide → HCID 70114961, compound

HRID 2393607Notes

Reaction equation

HRID 2393607 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([NH:12][C:13]1([CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:14]1=[O:27])=[O:11].[C:35](#[N:38])[CH:36]=[CH2:37].CN(C)C=O.[OH-].[Na+]>N12CCCN=C1CCCCC2.O.CO>[C:35]([CH2:36][CH2:37][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([NH:12][C:13]1([CH2:28][CH2:29][C:30]([OH:32])=[O:31])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:14]1=[O:27])=[O:11])#[N:38]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 7855AcrylonitrileHCID 14798Sodium HydroxideHCID 18976156HCID 18976156, compound

Product 1

HCID 70114961HCID 70114961, compoundYield 37.9%

Reagents, catalysts & solvents 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 375 mg of ethyl 3-[2,3-dihydro-3-(1H-indol-2-ylcarbonyl)amino-2-oxo-1-pentyl-1H-indol-3-yl]propionate, 530 mg of acrylonitrile, 3 drops of 1,8-diazabicyclo-[5.4.0]undec-7-ene (DBU) and 4 ml of dimethylformamide was stirred at 80° C. for 22 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. After the extract was washed, dried and then treated with activated charcoal, the solvent was removed by evaporation under reduced pressure to afford a caramel. A mixture of the residue obtained, 1.4 ml of an aqueous 2N sodium hydroxide solution and 10 ml of methanol was stirred at room temperature for 20 hours. After removal of methanol from the reaction mixture by evaporation under reduced pressure, the residue was made acidic with 10% hydrochloric acid and extracted with chloroform. After the extract was dried, the solvent was removed by evaporation under reduced pressure. The residue was recrystallized from diisopropyl ether to afford 150 mg of 3-[3-[1-(2-cyanoethyl)-1H-indol-2-ylcarbonylamino]-2,3-dihydro-2-oxo-1-pentyl-1H-indol-3-yl]propionic acid. Melting point 125° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter the extract was washed
  3. customdried
  4. additiontreated with activated charcoal
  5. customthe solvent was removed by evaporation under reduced pressure
  6. customto afford a caramel
  7. additionA mixture of the residue
  8. customobtained
  9. customAfter removal of methanol from the reaction mixture
  10. customby evaporation under reduced pressure
  11. extractionextracted with chloroform
  12. customAfter the extract was dried
  13. customthe solvent was removed by evaporation under reduced pressure
  14. customThe residue was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-75509232a9dc4d4ebbf01bb255816546
Source dataset
uspto-grants-1998_09
Patent number
US05807883

Reaction notes

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