Water → HCID 88137067, compound

HRID 1029491Notes

Reaction equation

HRID 1029491 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.[O:23]=[C:24]1[CH2:29][CH2:28][CH2:27][CH2:26][N:25]1[CH2:30][CH2:31][C:32]([OH:34])=[O:33].N12CCCN=C1CCCCC2.O>CN(C)C=O>[O:23]=[C:24]1[CH2:29][CH2:28][CH2:27][CH2:26][N:25]1[CH2:30][CH2:31][C:32]([O:34][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:33]

Participants

6

Reactant 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 141824043-Chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinoneHCID 199004253-(2-Oxopiperidin-1-yl)propanoic acid

Product 1

HCID 88137067HCID 88137067, compoundYield 46.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The procedure is as in Example 1, but starting with 3-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone (4,3 g) in anhydrous dimethylformamide (40 cc), 3-(2-oxopiperidino)propionic acid (2.2 g) and 1,8-diazabicyclo [5.4.0]undec-7-ene (2 g). After the reaction mixture has been taken up with water, the resulting mixture extracted with methylene chloride and the solvent evaporated, the residue obtained is recrystallized in acetonitrile. The product thereby obtained is purified by chromatography on silica (0.063-0.2 mm; 100 g) contained in a column 2.3 cm in diameter (eluant: methylene chloride), collecting 50-cc fractions. Fractions 56 to 64 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 20° C. The residue obtained is recrystallized in acetonitrile. 2-(7-Chloro-1,8-naphthridin-2-yl)-3-oxo-1-isoindolinyl 3-(2-oxopiperidino)propionate (2.8 g), m.p. 175° C., is thereby obtained.

Workup

  1. extractionthe resulting mixture extracted with methylene chloride
  2. customthe solvent evaporated
  3. customthe residue obtained
  4. customis recrystallized in acetonitrile
  5. customThe product thereby obtained
  6. customis purified by chromatography on silica (0.063-0.2 mm; 100 g)
  7. customcollecting 50-cc fractions
  8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 20° C
  9. customThe residue obtained
  10. customis recrystallized in acetonitrile

Sources & evidence

ORD record
ord-1126b0b6c86c4f70b415c5f0769d2929
Source dataset
uspto-grants-1992_04
Patent number
US05102890

Reaction notes

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