1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-(7-Chloro-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl 3-diisopropylaminopropionate

HRID 1029478Notes

Reaction equation

HRID 1029478 reaction equation
Cl[CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[N:15][C:16]([Cl:22])=[CH:17][CH:18]=2)[N:13]=1.Cl.[CH:24]([N:27]([CH:33]([CH3:35])[CH3:34])[CH2:28][CH2:29][C:30]([OH:32])=[O:31])([CH3:26])[CH3:25].N12CCCN=C1CCCCC2>CN(C)C=O>[CH:33]([N:27]([CH:24]([CH3:26])[CH3:25])[CH2:28][CH2:29][C:30]([O:32][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[N:15][C:16]([Cl:22])=[CH:17][CH:18]=2)[N:13]=1)=[O:31])([CH3:35])[CH3:34]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 141824043-Chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinoneHCID 867456233-Diisopropylaminopropionic acid hydrochloride

Product 1

HCID 199004232-(7-Chloro-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl 3-diisopropylaminopropionateYield 27.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Working as in Example 1, but starting with 3-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone (6.9 g) in anhydrous dimethylformamide (70 cc), 3-diisopropylaminopropionic acid hydrochloride (4.4 g) and 1,8-diazabicyclo-[5.4.0]undec-7-ene (7.45 g), and after the residue obtained has been recrystallized successively, first in acetonitrile and then in ethanol, 2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl 3-diisopropylaminopropionate (2.7 g), m.p. 135° C., is obtained.

Workup

  1. customafter the residue obtained
  2. customhas been recrystallized successively, first in acetonitrile

Sources & evidence

ORD record
ord-17f601b883ca47918467e3dd1059813b
Source dataset
uspto-grants-1992_04
Patent number
US05102890

Reaction notes

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