HCID 22175634, compound → HCID 22175773, compound

HRID 1797480Notes

Reaction equation

HRID 1797480 reaction equation
[CH2:1]([O:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([Cl:17])=[C:13]([Cl:16])[CH:14]=2)[C:9](=[O:18])[N:8]([CH2:19][CH2:20][C:21]([O:23]CC)=[O:22])[C:7]=1[CH2:26][N:27]1[C:35](=[O:36])[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]1=[O:37])[CH2:2][CH2:3][CH3:4]>Cl.C(O)(=O)C>[CH2:1]([O:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([Cl:17])=[C:13]([Cl:16])[CH:14]=2)[C:9](=[O:18])[N:8]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:7]=1[CH2:26][N:27]1[C:28](=[O:37])[C:29]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:35]1=[O:36])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 22175634HCID 22175634, compound

Product 1

HCID 22175773HCID 22175773, compoundYield 83.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

A mixture of ethyl 3-[4-butoxy-6,7-dichloro-3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-1-oxo-2 (1H)isoquinolinyl]propionate (1.36 g, 2.5 mmol) in 6N hydrochloric acid (15 ml) and acetic acid (15 ml) was refluxed with stirring for 2 h. The reaction mixture was concentrated under reduced pressure, and the residue was recrystallized from tetrahydrofuran-diisopropyl ether to give 3-[4-butoxy-6,7-dichloro-3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-1-oxo-2(1H)-isoquinolinyl]propionic acid (1.08 g, 83.7%) as crystals.

Workup

  1. temperaturewas refluxed
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was recrystallized from tetrahydrofuran-diisopropyl ether

Sources & evidence

ORD record
ord-075800992cd44a739138437ed804cfe8
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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