Water → HCID 19867667, compound

HRID 1199051Notes

Reaction equation

HRID 1199051 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]([OH:27])=O)=[N:10]2)=[CH:5][CH:4]=1.[CH2:28]([NH2:31])[CH2:29][CH3:30].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:31][CH2:28][CH2:29][CH3:30])=[O:27])=[N:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7852PropylamineHCID 19867644HCID 19867644, compound

Product 1

HCID 19867667HCID 19867667, compoundYield 107.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

N,N'-Carbonyldiimidazole (1.35 g) is added to a solution of [2-(7-methoxy-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyloxy]acetic acid (3 g) in anhydrous dimethylformamide (70 cc), and the mixture is stirred for 2 hours at a temperature in the region of 25° C. Propylamine (0.4 g) is then added and the mixture is stirred again for 16 hours at a temperature in the region of 25° C. The reaction mixture is then poured into water (150 cc) and the precipitate obtained is separated by filtration, washed with water, dried under reduced pressure (0.05 kPa) and recrystallized in ethanol. [2-(7-Methoxy-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyloxy]-N-propylacetamide (2.95 g), m.p. 174° C., is thereby obtained.

Workup

  1. stirringthe mixture is stirred again for 16 hours at a temperature in the region of 25° C
  2. customthe precipitate obtained
  3. customis separated by filtration
  4. washwashed with water
  5. customdried under reduced pressure (0.05 kPa)
  6. customrecrystallized in ethanol

Sources & evidence

ORD record
ord-60a6b6130f0f444184d1c4a837a1ccb5
Source dataset
uspto-grants-1990_02
Patent number
US04898871

Reaction notes

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