Sodium hydride → HCID 14209196, compound

HRID 1199035Notes

Reaction equation

HRID 1199035 reaction equation
[H-].[Na+].[OH:3][CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[N:5]1[C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[N:17][C:18]([O:24][CH3:25])=[CH:19][CH:20]=2)[N:15]=1.[CH3:26][N:27]([CH3:32])[C:28](=[O:31])[CH2:29]Cl>CN(C)C=O>[CH3:26][N:27]([CH3:32])[C:28](=[O:31])[CH2:29][O:13][CH:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4](=[O:3])[N:5]1[C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[N:17][C:18]([O:24][CH3:25])=[CH:19][CH:20]=2)[N:15]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 758862-chloro-N,N-dimethylacetamideHCID 141821812-(7-Methoxy-1,8-naphthyridin-2-yl)-3-hydroxy-1-isoindolinone

Product 1

HCID 14209196HCID 14209196, compoundYield 50.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Sodium hydride (0.25 g) is added in small portions at a temperature in the region of 0° C. to a solution, maintained under an argon atmosphere, of 3-hydroxy-2-(7-methoxy-1,8-naphthyridin-2-yl)-1-isoindolinone (3.1 g) in anhydrous dimethylformamide (50 cc). The suspension obtained is stirred for 45 minutes at a temperature in the region of 0° C., and N,N-dimethyl-2chloroacetamide (1.3 g) is then added. The reaction mixture is heated with stirring to a temperature of 70° C. for 3 hours, then cooled to a temperature in the region of 10° C., poured into distilled water (200 cc) and extracted with dichloromethane (3×70 cc). The organic phases are combined, washed with distilled water (2×40 cc), dried over magnesium sulphate, filtered and then concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization in ethyl acetate, N,N-dimethyl-2-[2-(7-methoxy-1,8-naphthyridin-2-yl)- 3-oxo-1 -isoindolinyloxy]acetamide (2 g), m.p. 166° C., is obtained.

Workup

  1. customThe suspension obtained
  2. additionis then added
  3. temperatureThe reaction mixture is heated
  4. temperaturecooled to a temperature in the region of 10° C.
  5. additionpoured
  6. distillationinto distilled water (200 cc)
  7. extractionextracted with dichloromethane (3×70 cc)
  8. washwashed with distilled water (2×40 cc)
  9. dry with materialdried over magnesium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  12. customAfter recrystallization in ethyl acetate

Sources & evidence

ORD record
ord-62f95303221644c1991c2a853fb68a9a
Source dataset
uspto-grants-1990_02
Patent number
US04898871

Reaction notes

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