Water → HCID 22163850, compound

HRID 1087784Notes

Reaction equation

HRID 1087784 reaction equation
[Cl-].[Li+].O.[Cl:4][C:5]1[N:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([N:15]3[C:23](=[O:24])[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]3[CH:25]([C:30](=[O:38])[CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)C(OC)=O)=[N:12]2)=[CH:7][CH:6]=1>CS(C)=O>[Cl:4][C:5]1[N:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([N:15]3[CH:16]([CH2:25][C:30](=[O:38])[CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:17]4[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:23]3=[O:24])=[N:12]2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 433294Lithium ChlorideHCID 22163844HCID 22163844, compound

Product 1

HCID 22163850HCID 22163850, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Lithium chloride (4.2 g) and water (1.8 cc) are added at a temperature in the region of 20° C. to a solution, maintained under an argon atmosphere, of methyl 2-[2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl]-3-oxo-4-phenylbutanoate (3 g) in dimethyl sulphoxide (230 cc), and the reaction mixture is heated to reflux for 45 minute$. After the mixture is cooled to a temperature in the region of 40° C., ice-cold water (1500 cc) is added. After 15 minutes.varies. stirring, the solid which precipitates is separated by filtration, washed with distilled water (5×25 cc) and dried in the air. The solid obtained is purified by chromatography on silica gel (140 g) contained in a column 3.4 cm in diameter (eluent: dichloromethane/methanol (98:2 by volume)]. Elution is first performed with 200 cc of solvent: the corresponding eluate is discarded. Elution is then performed with 900 cc of solvent: the corresponding eluate is concentrated to dryness under reduced pressure (2.7 kPa), at 40° C. After recrystallization in acetonitrile, 2-(7-chloro-1,8-naphthyridin-2-yl)-3-(3-phenyl-2-oxopropyl)-1-isoindolinone (1.2 g), m.p. 182° C., is obtained.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureto reflux for 45 minute$
  3. additionis added
  4. customthe solid which precipitates
  5. customis separated by filtration
  6. washwashed with distilled water (5×25 cc)
  7. customdried in the air
  8. customThe solid obtained
  9. customis purified by chromatography on silica gel (140 g)
  10. washElution
  11. washElution
  12. concentrationthe corresponding eluate is concentrated to dryness under reduced pressure (2.7 kPa), at 40° C
  13. customAfter recrystallization in acetonitrile

Sources & evidence

ORD record
ord-f52e7b330eb847e988a285fe617e4455
Source dataset
uspto-grants-1990_10
Patent number
US04960779

Reaction notes

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