HCID 68542093, compound → HCID 23085215, compound

HRID 1442582Notes

Reaction equation

HRID 1442582 reaction equation
[C:1]([NH:9][C:10](=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]#[N:23])[CH:17]=1)[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCCC1.[Pd]>[C:1]([NH:9][CH:10]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]#[N:23])[CH:17]=1)[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 68542093HCID 68542093, compound

Product 1

HCID 23085215HCID 23085215, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of methyl 2-(benzoylamino)-3-(3-cyanophenyl)2-propenoate (300 mg, 0.979 mmol) and 5% palladium/barium sulfate (60 mg) in tetrahydrofuran (3 mL) was stirred at 50° C. for 7.5 hours under a hydrogen flow. The catalyst was filtered off and the filtrate was concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (3 mL) and 5% palladium/barium sulfate (90 mg) was added to the solution. The mixture was stirred at 50° C. for 8 hours under a hydrogen flow. The catalyst was filtered off and the filtrate was concentrated under reduced pressure. The residue was crystallized from ethyl acetate-hexane to give the title compound (273 mg, 90%).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in tetrahydrofuran (3 mL)
  4. addition5% palladium/barium sulfate (90 mg) was added to the solution
  5. stirringThe mixture was stirred at 50° C. for 8 hours under a hydrogen flow
  6. filtrationThe catalyst was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-dfc3199771f74b68b1d3517f964eeb3e
Source dataset
uspto-grants-2010_02
Patent number
US07659267B2

Reaction notes

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