Triethylamine → HCID 59574232, compound

HRID 2092034Notes

Reaction equation

HRID 2092034 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][C:7]=1[CH:8]([N:11]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]1=[O:21])[CH2:9][CH3:10].C(N(CC)CC)C.[H][H]>O1CCCC1.[C].[Pd]>[N:4]1[CH:5]=[CH:6][C:7]([CH:8]([N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])[CH2:9][CH3:10])=[CH:2][N:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 59574209HCID 59574209, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59574232HCID 59574232, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-[1-(3,6-Dichloropyridazin-4-yl)propyl]isoindoline-1,3-dione, triethylamine (1.11 mL, 8 mmol) and 10% palladium-carbon (50 wt %, 100 mg) were stirred in tetrahydrofuran in a hydrogen atmosphere (1 atm) at room temperature for 4 days. The reaction solution was filtered through celite and concentrated under reduced pressure, and the resulting residue was dissolved in chloroform, and the resulting organic layer was washed with water and saturated aqueous sodium hydrogen carbonate, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/3) to give the desired product (294 mg, 28% yield, two steps).

Workup

  1. filtrationThe reaction solution was filtered through celite and
  2. concentrationconcentrated under reduced pressure
  3. dissolutionthe resulting residue was dissolved in chloroform
  4. washthe resulting organic layer was washed with water and saturated aqueous sodium hydrogen carbonate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/3)

Sources & evidence

ORD record
ord-de0ab25801d6488198355993b5faf9c2
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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