Water → HCID 19867686, compound

HRID 1199049Notes

Reaction equation

HRID 1199049 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][NH2:6].[OH:8][CH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=O)[N:10]1[C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[N:22][C:23]([O:29][CH3:30])=[CH:24][CH:25]=2)[N:20]=1.O.C(OCC)(=O)C>CN(C)C=O>[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][NH:6][CH:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9](=[O:8])[N:10]1[C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[N:22][C:23]([O:29][CH3:30])=[CH:24][CH:25]=2)[N:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7993N,N-Dimethyl-1,3-propanediamineHCID 8857Ethyl AcetateHCID 141821812-(7-Methoxy-1,8-naphthyridin-2-yl)-3-hydroxy-1-isoindolinone

Product 1

HCID 19867686HCID 19867686, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Dimethylaminopropylamine (5.1 g) is added at a temperature in the region of 20° C. to a solution of 3-hydroxy-2-(7-methoxy-1,8-naphthyridin-2-yl)-1-isoindolinone (12.4 g) in anhydrous dimethylformamide (200 cc), and the reaction mixture is heated to reflux for 8 hours. After being cooled, the reaction mixture is poured into a mixture of water (1200 cc) and ethyl acetate (500 cc) and filtered to remove an insoluble product. The aqueous phase is separated after settling has occurred and then extracted with ethyl acetate (2×250 cc). The organic phases are combined, washed with water (5×80 cc), dried over magnesium sulphate, filtered and then concentrated to dryness under reduced pressure (2.7 kPa) at 60° C. After recrystallization in ethyl acetate, 3-(3-dimethylaminopropylamino)-2-(7-methoxy-1,8-naphthyridin-2-yl)-1-isoindolinone (5.1 g), m.p. 128° C., is obtained.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureto reflux for 8 hours
  3. temperatureAfter being cooled
  4. filtrationfiltered
  5. customto remove an insoluble product
  6. customThe aqueous phase is separated after settling
  7. extractionextracted with ethyl acetate (2×250 cc)
  8. washwashed with water (5×80 cc)
  9. dry with materialdried over magnesium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 60° C
  12. customAfter recrystallization in ethyl acetate

Sources & evidence

ORD record
ord-cbe40c3dff8946cca7d27f775e8c61fe
Source dataset
uspto-grants-1990_02
Patent number
US04898871

Reaction notes

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