Water → HCID 19867663, compound

HRID 1199054Notes

Reaction equation

HRID 1199054 reaction equation
[CH3:1][O:2][C:3]1[N:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([N:13]3[C:21](=[O:22])[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]3[O:23][CH2:24][C:25](O)=[O:26])=[N:10]2)=[CH:5][CH:4]=1.[CH3:28][N:29]([CH3:33])[CH2:30][CH2:31][NH2:32].O>CN(C)C=O>[CH3:1][O:2][C:3]1[N:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([N:13]3[C:21](=[O:22])[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]3[O:23][CH2:24][C:25]([NH:32][CH2:31][CH2:30][N:29]([CH3:33])[CH3:28])=[O:26])=[N:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 66053N,N-DimethylethylenediamineHCID 19867644HCID 19867644, compound

Product 1

HCID 19867663HCID 19867663, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N'-Carbonyldiimidazole (1.8 g) is added at a temperature in the region of 25° C. to a solution of [2-(7-methoxy-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyloxy]acetic acid (4 g) in anhydrous dimethylformamide (85 cc), and the mixture is stirred for 2 hours at this temperature. 2-Dimethylaminoethylamine (0.7 g) is then added and the mixture is stirred for 18 hours at this same temperature. The reaction mixture is then poured into water (200 cc) and extracted with methylene chloride (3×200 cc). The organic extracts are washed with water, dried and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. The residue obtained is crystallized by stirring in ethyl ether. [2-(7-Methoxy-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyloxy]-N-(2-dimethylamino ethyl)acetamide (3.5 g), m.p. 146° C., is thereby obtained.

Workup

  1. stirringthe mixture is stirred for 18 hours at this same temperature
  2. extractionextracted with methylene chloride (3×200 cc)
  3. washThe organic extracts are washed with water
  4. customdried
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  6. customThe residue obtained
  7. customis crystallized
  8. stirringby stirring in ethyl ether

Sources & evidence

ORD record
ord-028da9bda18e4244885f095c8421f4f7
Source dataset
uspto-grants-1990_02
Patent number
US04898871

Reaction notes

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