Glutaric anhydride → HCID 69155680, compound

HRID 750302Notes

Reaction equation

HRID 750302 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([Br:21])=[CH:10][CH:9]=2)=[O:4].C(N(CC)CC)C.[C:38]1(=[O:45])[O:44][C:42](=[O:43])[CH2:41][CH2:40][CH2:39]1>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:25]=[CH:26][C:27]([NH:30][C:38](=[O:45])[CH2:39][CH2:40][CH2:41][C:42]([OH:44])=[O:43])=[CH:28][CH:29]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[CH:12][C:11]([Br:21])=[CH:10][CH:9]=2)=[O:4]

Participants

5

Reactant 3

HCID 7940Glutaric anhydrideHCID 8471TriethylamineHCID 44451607HCID 44451607, compound

Product 1

HCID 69155680HCID 69155680, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-aminobenzyl)-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (139 mg) in tetrahydrofuran (5 ml) were added triethylamine (0.084 ml), glutaric anhydride (51 mg), and the mixture was stirred at room temperature for 24 hrs. The solvent was evaporated under reduced pressure, water was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried by adding sodium sulfate. The solvent was evaporated under reduced pressure and isopropyl ether was added to the obtained residue and the mixture was crystallized. The obtained crystals were collected by filtration and dried under reduced pressure at 50° C. to give the title compound (131 mg, 76%).

Workup

  1. customThe solvent was evaporated under reduced pressure, water
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. customdried
  6. additionby adding sodium sulfate
  7. customThe solvent was evaporated under reduced pressure and isopropyl ether
  8. additionwas added to the obtained residue
  9. customthe mixture was crystallized
  10. filtrationThe obtained crystals were collected by filtration
  11. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-93450352032e4c2b9b3d95b6ac4cb723
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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